Organic EL device

ABSTRACT

In an organic EL device comprising organic layers between a pair of electrodes participating in at least a light emitting function, at least one organic layer contains an organic compound selected from naphthacene, tetraaryldiamine, anthracene and quinoxaline derivatives as a host material and an organic compound having a specific skeleton, typically diindeno[1,2,3-cd:1′,2′,3′-lm]perylene derivative as a dopant. The device is capable of light emission to a satisfactory luminance, especially in a long wavelength region, and with a chromatic purity sufficient for use in full color displays, and had a sufficient durability to sustain such improved light emission performance over a long time.

BACKGROUND OF THE INVENTION

[0001] 1. Field of the Invention

[0002] This invention relates to an organic electroluminescent (EL)device, and more particularly, to a compound for use in a device of thetype wherein an electric field is applied across a thin film of anorganic compound to emit light.

[0003] 2. Background Art

[0004] Organic electroluminescent (EL) devices include a thin filmcontaining a luminescent organic compound interleaved between anelectron injecting electrode and a hole injecting electrode. Electronsand holes are injected into the thin film where they are recombined tocreate excitons. Light is emitted by utilizing luminescence(phosphorescence or fluorescence) upon deactivation of excitons.

[0005] The organic EL devices are characterized by plane light emissionat a high luminance of about 100 to 10,000 cd/m² with a voltage of about10 volts and light emission in a spectrum from blue to red color by asimple choice of the type of fluorescent material.

[0006] Doping is one technique for producing light emission of anydesired color from organic EL devices. It was reported in Jpn. J. Appl.Phys., 10, 527 (1971) to change emission color from blue to green bydoping anthracene crystals with a minor level of tetracene. With respectto organic thin film EL devices having a multilayer structure, it wasreported in JP-A 63-264692 to incorporate in a host material having alight emitting function a minor amount of a fluorescent dye capable ofemitting light different from that of the host material in response tolight emission from the host material as a dopant to form a lightemitting layer, thereby changing the color of light emission from greento orange or red.

[0007] With respect to long wavelength light emission of yellow to red,known light emitting materials or dopant materials include laser dyescapable of red oscillation (EPO 281381), compounds capable of exciplexemission (JP-A 2-255788), perylene compounds (JP-A 3-791), coumarincompounds (JP-A 3-792), dicyanomethylene compounds (JP-A 3-162481),thioxanthene compounds (JP-A 3-177486), mixtures of a conjugated polymerand an electron transporting compound (JP-A 6-73374), squaliriumcompounds (JP-A 6-93257), oxadiazole compounds (JP-A 6-136359), oxynatederivatives (JP-A 6-145146), and pyrene compounds (JP-A 6-240246).

[0008] It is reported in J. Am. Chem. Soc., 118, 2374-2379, 1996, thatbenzofluoranthene derivatives have a very high fluorescent quantumyield. JP-A 10-330295 and JP-A 11-233261 disclose organic EL deviceshaving a light emitting layer in which a variety of host materials aredoped with dibenzo[f,f′]diindeno[1,2,3-cd:1′,2′,3′-lm]perylenederivatives derived from benzofluoranthene.

[0009] Other light emitting materials disclosed heretofore includecondensed polycyclic aromatic compounds (JP-A 5-32966 and 5-214334).Also dopant materials proposed heretofore include various condensedpolycyclic aromatic compounds (JP-A 5-258859).

[0010] However, when these materials are used as the dopant, EL devicesoften fail to allow dopant molecules to exert their own fluorescence dueto the interaction between dopants or between the dopant and the host.

[0011] Therefore, with respect to organic EL devices of the type inwhich a host material is doped with a fluorescent dye, a choice of hostmaterial is an important and difficult task in order for the device toproduce high efficiency light emission. Currently available organic ELdevices fail to reach a practically acceptable level of emissionefficiency although fluorescent dyes having a high fluorescent quantumyield are used as the dopant.

[0012] When organic EL devices are fabricated using the dopingtechnique, the energy transfer from host molecules in the excited stateto the dopant is not 100%, and often not only the dopant, but also thehost material emit light. Especially in the case of red light emittingdevices, the chromatic purity is often exacerbated by faint lightemission of the host material since the host material emits light in awavelength region of higher visibility than the dopant. Furtherimprovements in properties pertaining to the luminous lifetime anddurability are needed, with the target placed on practical application.

SUMMARY OF THE INVENTION

[0013] An object of the invention is to provide an organic EL devicecapable of light emission to a satisfactory luminance, especially in along wavelength region, and with a chromatic purity sufficient for usein full color displays, and having a sufficient durability to sustainsuch improved light emission performance over a long time.

[0014] The above and other objects are achieved by the invention whichis defined below.

[0015] [1] An organic EL device comprising one or more organic layersbetween a pair of electrodes participating in at least a light emittingfunction,

[0016] at least one of the organic layers containing at least one oforganic compounds having basic skeletons of the following formulas (I)to (IV) and at least one organic compound having a skeleton of thefollowing formula (V) at the same time:

[0017]  wherein Q¹ to Q⁸ are independently hydrogen or substituted orunsubstituted alkyl, aryl, amino, heterocyclic or alkenyl radicals,

[0018]  wherein R₁, R₂, R₃ and R₄ are independently aryl, fluorene,carbazolyl, alkyl, alkoxy, aryloxy, amino or halogen radicals, at leastone of R₁, R₂, R₃ and R₄ is aryl, r1, r2, r3 and r4 each are 0 or aninteger of 1 to 5, with the proviso that r1, r2, r3 and r4 are not 0 atthe same time, R₅ and R₆ are independently alkyl, alkoxy, amino, aryl orhalogen radicals and may be the same or different, r5 and r6 each are 0or an integer of 1 to 4,

[0019]  wherein A₁₀₁ is a monophenylanthryl or diphenylanthryl radicaland may be the same or different, L is hydrogen, a single bond or ann-valent linkage, and n is an integer of 1 to 4,

Q_(n)-L₁₀₁  (IV)

[0020]  wherein Q is a pyrazinyl radical having fused thereto asix-membered aromatic ring containing 0 to 2 nitrogen atoms and may bethe same or different, n is 2 or 3, and L₁₀₁ is a single bond orn-valent radical,

[0021]  wherein X₁ to X₁₀, L₁ and L₂ are independently hydrogen, halogenatoms, straight, branched or cyclic alkyl radicals which may havesubstituents, straight, branched or cyclic alkoxy radicals which mayhave substituents, straight, branched or cyclic alkylthio radicals whichmay have substituents, straight, branched or cyclic alkenyl radicalswhich may have substituents, straight, branched or cyclic alkenyloxyradicals which may have substituents, straight, branched or cyclicalkenylthio radicals which may have substituents, substituted orunsubstituted aralkyl radicals, substituted or unsubstituted aralkyloxyradicals, substituted or unsubstituted aralkylthio radicals, substitutedor unsubstituted aryl radicals, substituted or unsubstituted aryloxyradicals, substituted or unsubstituted arylthio radicals, substituted orunsubstituted amino radicals, cyano, hydroxyl, —COOR¹ radicals (whereinR¹ is hydrogen, a substituted or unsubstituted straight, branched orcyclic alkyl radical, a substituted or unsubstituted straight, branchedor cyclic alkenyl radical, a substituted or unsubstituted aralkylradical or a substituted or unsubstituted aryl radical), —COR² radicals(wherein R² is hydrogen, a substituted or unsubstituted straight,branched or cyclic alkyl radical, a substituted or unsubstitutedstraight, branched or cyclic alkenyl radical, a substituted orunsubstituted aralkyl radical, a substituted or unsubstituted arylradical or an amino radical), or —OCOR³ radicals (wherein R³ is asubstituted or unsubstituted straight, branched or cyclic alkyl radical,a substituted or unsubstituted straight, branched or cyclic alkenylradical, a substituted or unsubstituted aralkyl radical, or asubstituted or unsubstituted aryl radical), or at least two adjoiningradicals selected from X₁ to X₁₀, L₁ and L₂ may bond or fuse together toform a substituted or unsubstituted carbocyclic aliphatic ring, aromaticring or fused aromatic ring with the carbon atoms to which they areattached, or L₁ and L₂ each may be a single bond. n is 1 or 2.

[0022] [2] The organic EL device of [1] wherein the at least one of theorganic layers contains a host material and a dopant,

[0023] said host material comprises at least one compound selected fromthe organic compounds having basic skeletons of the formulas (I) to (IV)and

[0024] said dopant comprises at least one compound selected from theorganic compounds having a skeleton of the formula (V).

[0025] [3] The organic EL device of [1] or [2] wherein in formula (V),at least two adjoining radicals selected from X₁ to X₁₀, L₁ and L₂ bondor fuse together to form a substituted or unsubstituted carbocyclicaliphatic ring, aromatic ring or fused aromatic ring with the carbonatoms to which they are attached.

[0026] [4] The organic EL device of any one of [1] to [3] wherein thecompound of formula (V) is a compound of the following formula (VI):

[0027] wherein X₁ to X₆, X₉, X₁₀, X₁₁ to X₁₆, X₁₉ and X₂₀ areindependently hydrogen, halogen atoms, straight, branched or cyclicalkyl radicals which may have substituents, straight, branched or cyclicalkoxy radicals which may have substituents, straight, branched orcyclic alkylthio radicals which may have substituents, straight,branched or cyclic alkenyl radicals which may have substituents,straight, branched or cyclic alkenyloxy radicals which may havesubstituents, straight, branched or cyclic alkenylthio radicals whichmay have substituents, substituted or unsubstituted aralkyl radicals,substituted or unsubstituted aralkyloxy radicals, substituted orunsubstituted aralkylthio radicals, substituted or unsubstituted arylradicals, substituted or unsubstituted aryloxy radicals, substituted orunsubstituted arylthio radicals, substituted or unsubstitutedarylalkenyl radicals, substituted or unsubstituted alkenylaryl radicals,substituted or unsubstituted amino radicals, cyano, hydroxyl, —COOR¹radicals (wherein R¹ is hydrogen, a substituted or unsubstitutedstraight, branched or cyclic alkyl radical, a substituted orunsubstituted straight, branched or cyclic alkenyl radical, asubstituted or unsubstituted aralkyl radical or a substituted orunsubstituted aryl radical), —COR² radicals (wherein R² is hydrogen, asubstituted or unsubstituted straight, branched or cyclic alkyl radical,a substituted or unsubstituted straight, branched or cyclic alkenylradical, a substituted or unsubstituted aralkyl radical, a substitutedor unsubstituted aryl radical or an amino radical), or —OCOR³ radicals(wherein R³ is a substituted or unsubstituted straight, branched orcyclic alkyl radical, a substituted or unsubstituted straight, branchedor cyclic alkenyl radical, a substituted or unsubstituted aralkylradical, or a substituted or unsubstituted aryl radical), or at leasttwo adjoining radicals selected from X₁ to X₂₀ may bond together to forma substituted or unsubstituted carbocyclic aliphatic ring, aromatic ringor fused aromatic ring with the carbon atoms to which they are attached.

[0028] [5] The organic EL device of [4] wherein the compound of formula(VI) is a compound of the following formula (VI′):

[0029] wherein X₁ to X₄₄ are as defined for X₁ to X₂₀ in formula (VI).

[0030] [6] The organic EL device of [4] or [5] wherein X₁ to X₂₀ informula (VI) and X₁ to X₄₄ in formula (VI′) are independentlysubstituted or unsubstituted aryl, alkyl, alkenyl, alkoxy or aryloxyradicals.

[0031] [7] The organic EL device of any one of [4] to [6] wherein atleast one of X₁ to X₂₀ in formula (VI) and X₁ to X₄₄ in formula (VI′) isan ortho-substituted phenyl radical. [8] The organic EL device of anyone of [4] to [7] wherein in formula (VI) or (VI′), either one or bothof X₁ and X₄ and/or either one or both of X₁₁ and X₁₄ areortho-substituted phenyl radicals.

[0032] [9] The organic EL device of any one of [1] to [8] wherein saidat least one of the organic layers contains at least one organiccompound having a basic skeleton of the formula (I).

[0033] [10] The organic EL device of any one of [1] to [9] wherein saidat least one of the organic layers contains at least one organiccompound having a basic skeleton of the formula (I) and at least oneorganic compound having a basic skeleton of the formula (II) at the sametime.

[0034] [11] The organic EL device of any one of [4] to [10] wherein atleast one of the organic compounds has a vibration structure in both anexcitation spectrum and a fluorescence spectrum.

[0035] [12] The organic EL device of any one of [4] to [11] wherein atleast one of the organic compounds has a Stokes shift of up to 0.1 eV.

[0036] [13] The organic EL device of any one of [4] to [12] wherein thehost material in a light emitting layer has a greater electron affinitythan an electron transporting layer and/or a hole transporting layer.

[0037] [14] The organic EL device of any one of [1] to [13] wherein theorganic compound having a basic skeleton of the formula (I) is onewherein at least two of Q¹ to Q⁸ are substituted or unsubstituted arylradicals.

[0038] [15] The organic EL device of [14] wherein the organic compoundhaving a basic skeleton of the formula (I) is one wherein at least sixof Q¹ to Q⁸ are substituted or unsubstituted aryl radicals.

[0039] [16] The organic EL device of [14] or [15] wherein the organiccompound having a basic skeleton of the formula (I) is one wherein atleast two of Q¹, Q², Q³ and Q⁴ are substituted or unsubstituted arylradicals.

[0040] [17] The organic EL device of any one of [14] to [16] wherein theorganic compound having a basic skeleton of the formula (I) is onewherein at least four of Q¹, Q², Q³ and Q⁴ are substituted orunsubstituted aryl radicals.

[0041] [18] The organic EL device of any one of [14] to [17] wherein atleast two of the aryl radicals represented by Q¹, Q², Q³ and Q⁴ havearyl radicals substituted thereon.

[0042] [19] The organic EL device of any one of [2] to [18] wherein theat least one of the organic layers contains 80 to 99.9% by weight of thehost material.

[0043] [20] An organic EL device wherein at least one of organic layerscontains at least one organic compound having a basic skeleton of theformula (I) as set forth in [16] and at least one organic compoundhaving a basic skeleton of the formula (IV′).

[0044] [21] The organic EL device of any one of [1] to [20], furthercomprising at least one hole injecting and transporting layer.

[0045] [22] The organic EL device of any one of [1] to [21], furthercomprising at least one electron injecting and transporting layer.

[0046] [23] An organic EL device comprising one or more organic layersbetween a pair of electrodes participating in at least a light emittingfunction, wherein the one or more organic layers contain organiccompounds, at least one of which has a vibration structure in both anexcitation spectrum and a fluorescence spectrum.

[0047] [24] An organic EL device comprising one or more organic layersbetween a pair of electrodes participating in at least a light emittingfunction, wherein the one or more organic layers contain organiccompounds, at least one of which has a Stokes shift of up to 0.1 eV.

[0048] [25] The organic EL device of [24] wherein a host material in alight emitting layer has a greater electron affinity than an electrontransporting layer and/or a hole transporting layer.

BRIEF DESCRIPTION OF THE DRAWINGS

[0049]FIG. 1 is a schematic cross-sectional view showing the basicconstruction of an organic EL device according to the invention.

[0050]FIG. 2 is a diagram showing the excitation and fluorescencespectra of the host material and dopant used in Example.

[0051]FIG. 3 is a diagram showing the excitation and fluorescencespectra of the host material and dopant used in Comparative Example.

DESCRIPTION OF THE PREFERRED EMBODIMENT

[0052] According to the invention, an organic EL device having a highluminous efficiency and a long lifetime is obtained by combining anorganic compound of formula (V) or (VI) with at least one of organiccompounds of formulas (I) to (IV), especially by combining an organiccompound of formula (V) or (VI) as a dopant with an organic compound offormula (I) as a host material. First the organic compounds useful asthe host material are described in detail.

[0053] Host Materials

[0054] Naphthacene Compounds

[0055] One class of organic compounds useful as the host materialaccording to the invention have a basic skeleton of the followingformula (I).

[0056] In the device of the invention, the use of the naphthacenederivative, preferably as the host material, helps induce strong lightemission from the dopant.

[0057] Naphthacene derivatives belong to a class of preferable organiccompounds, especially effective as the host material, among others. Forexample, the fluorescence intensity of a film of a naphthacenederivative of host material in example 1 doped with 1 wt % of adibenzo[f,f′]diindeno[1,2,3-cd:1′,2′,3′-lm]perylene derivative of dopantmaterial in Example 1, as measured on photoexcitation, is about 2 timesthe fluorescence intensities of films of other organic compounds (e.g.,Alq3) as the host.

[0058] The reason why such intense fluorescence is produced ispresumably that the combination of a naphthacene derivative with theabove dopant is an ideal combination that avoids interaction such asformation of an exciplex, and bipolar interaction between the respectivemolecules maintains a high intensity of fluorescence.

[0059] In the event of a red dopant, since the energy gap of anaphthacene derivative is relatively approximate to that of the dopant,an energy transfer phenomenon due to emission resorption takes place aswell as energy transfer by electron exchange. This accounts for a highfluorescence intensity as well.

[0060] The combination with the above host material minimizes theconcentration quenching of the dopant, which also accounts for a highfluorescence intensity.

[0061] In an exemplary organic EL device which was fabricated using theabove doped film as a light emitting layer, a luminance of at least 600cd/m² at maximum was obtained at a current density of 10 mA/cm² and adrive voltage as low as about 6 V. When operated at a current density ofabout 600 mA/cm², the device consistently produced a luminance ofgreater than about 20,000 cd/m². As compared with other organiccompounds (e.g., Alq3) serving as the host, this provides a luminousefficiency greater by a factor of about 4 when assessed in terms ofcurrent efficiency, and because of possible driving at a lower voltage,a luminous efficiency greater by a factor of about 5 when assessed interms of power efficiency. In the event of doping with a red dopant asin the above example, entailing the high efficiency of energy transferfrom the host to the dopant, the device is characterized by a highchromatic purity in that only the dopant produces light emission, withlittle light emission from the host being observable.

[0062] It is believed that such a very high luminous efficiency exertedwhen organic EL devices are fabricated is due to the effects of animproved recombination probability of carriers in the light emittinglayer and a singlet excitation state that the dopant forms as a resultof energy transfer from the triplet excitation state of naphthacene, aswell as the above-mentioned mechanism of providing a high fluorescenceintensity.

[0063] As opposed to conventional organic EL devices whose drive voltageis increased by carrier trapping of the dopant, the inventive organic ELdevice using the above-mentioned light emitting layer has a very lowdrive voltage, because the order of carrier trapping of the dopant islow and high efficiency light emission is accomplished by theabove-mentioned mechanism. Another accomplished by the above-mentionedmechanism. Another probable reason is the ease of injection of carriersinto the light emitting layer.

[0064] Since the naphthacene derivative is very stable and highlydurable against carrier injection, the device fabricated using the abovehost-dopant combination has a very long lifetime. For example, anorganic EL device having a light emitting layer of a compound of formula(VII′) doped with 1 wt % of adibenzo[f,f′]diindeno[1,2,3-cd:1′,2′,3′-lm]perylene derivative of dopantmaterial in Example 1 is highly durable as demonstrated by its abilityto sustain a luminance of at least 2,400 cd/m² over a period of 1,000hours or longer, with an attenuation of less than about 1%, when drivenat 50 mA/cm².

[0065] In organic EL devices as mentioned above, the dopantconcentration ensuring a chromatic purity and maximum efficiency isabout 1% by weight although dopant concentrations of about 2 or 3% byweight lead to devices which are practically acceptable albeit a drop ofless than about 10%.

[0066] In formula (I), Q¹ to Q⁴ are independently selected from amonghydrogen and substituted or unsubstituted alkyl, aryl, amino,heterocyclic and alkenyl radicals. Preferred are aryl, amino,heterocyclic and alkenyl radicals. It is also desirable that Q² and Q³are these preferred radicals and Q¹ and Q⁴ are hydrogen.

[0067] The aryl radicals represented by Q¹ to Q⁴ may be monocyclic orpolycyclic, inclusive of fused rings and a collection of rings. Thosearyl radicals having 6 to 30 carbon atoms in total are preferred andthey may have substituents. Preferred examples of the aryl radicalinclude phenyl, o-, m- and p-tolyl, pyrenyl, perylenyl, coronenyl, 1-and 2-naphthyl, anthryl, o-, m- and p-biphenylyl, terphenyl andphenanthryl.

[0068] The amino radicals represented by Q¹ to Q⁴ may be selected fromamong alkylamino, arylamino, aralkylamino and analogous radicals. Theypreferably have aliphatic radicals having 1 to 6 carbon atoms in totaland/or aromatic carbocyclic radicals having 1 to 4 rings. Illustrativeexamples include dimethylamino, diethylamino, dibutylamino,diphenylamino, ditolylamino, bisdiphenylylamino, and bisnaphthylaminoradicals.

[0069] The heterocyclic radicals represented by Q¹ to Q⁴ include 5- or6-membered ring aromatic heterocyclic radicals containing O, N or S as ahetero atom, and fused polycyclic aromatic heterocyclic radicals having2 to 20 carbon atoms. Examples of the aromatic heterocyclic radicals andfused polycyclic aromatic heterocyclic radicals include thienyl, furyl,pyrolyl, pyridyl, quinolyl, and quinoxalyl radicals.

[0070] The alkenyl radicals represented by Q¹ to Q⁴ are preferably thosehaving a phenyl group as at least one substituent, such as 1- and2-phenylalkenyl, 1,2- and 2,2-diphenylalkenyl, and1,2,2-triphenylalkenyl although unsubstituted alkenyl radicals areacceptable.

[0071] When Q¹ to Q⁴ are substituted radicals, at least two of thesubstituents are preferably aryl, amino, heterocyclic, alkenyl oraryloxy groups. These aryl, amino, heterocyclic and alkenyl groups areas illustrated above for Q¹ to Q⁴. The aryloxy groups to substitute onQ¹ to Q⁴ are preferably those of aryl groups having 6 to 18 carbon atomsin total, for example, o-, m- and p-phenoxy. At least two of thesesubstituents may form a fused ring. Also, these substituents may befurther substituted ones, in which preferred substituents are asdescribed above.

[0072] When Q¹ to Q⁴ have substituents, it is preferred that at leasttwo of the substituents have the above-described substituents. Theposition of substitution is not particularly limited and may be a meta,para or ortho position. Q¹ and Q⁴, and Q² and Q³ in the respective pairsare preferably identical although they may be different.

[0073] Q⁵ to Q⁸ are independently selected from among hydrogen andsubstituted or unsubstituted alkyl, aryl, amino, heterocyclic andalkenyl radicals.

[0074] The alkyl radicals represented by Q⁵ to Q⁸ are preferably thoseof 1 to 6 carbon atoms, which may be straight or branched. Preferredexamples of the alkyl radical include methyl, ethyl, n- and i-propyl,n-, i-, sec- and tert-butyl, n-, i-, neo- and tert-pentyl.

[0075] The aryl, amino and alkenyl radicals represented by Q⁵ to Q⁸ areas illustrated above for Q¹ to Q⁴. Q⁵ and Q⁶, and Q⁷ and Q⁸ in therespective pairs are preferably identical although they may bedifferent.

[0076] It is preferred that rubrene of formula (I) wherein all Q¹ to Q⁴are phenyl and all Q⁵ to Q⁸ are hydrogen be excluded.

[0077] The naphthacene derivative contained in the light emitting layershould preferably have a basic skeleton of the following formula (VII).

[0078] In formula (VII), Q¹¹ to Q¹³, Q²¹ to Q²³, Q³¹ to Q³³ and Q⁴¹ toQ⁴³ are hydrogen, aryl, amino, heterocyclic, aryloxy or alkenylradicals. Preferably the Q's in at least one of these sets are radicalshaving substituents selected from among aryl, amino, heterocyclic andaryloxy groups. Two or more of these Q's may form a fused ring.

[0079] Preferred examples of the aryl, amino, heterocyclic and aryloxyradicals are as exemplified above for Q¹ to Q⁴. Preferably Q¹¹ to Q¹³and Q⁴¹ to Q⁴³, and Q²¹ to Q²³ and Q³¹ to Q³³ in the respective pairedsets are identical although they may be different.

[0080] The amino groups substituting on Q¹¹ to Q¹³, Q²¹ to Q²³, Q³¹ toQ³³ and Q⁴¹ to Q⁴³ may be selected from among alkylamino, arylamino,aralkylamino and analogous groups. They preferably have aliphatic groupshaving 1 to 6 carbon atoms in total and/or aromatic carbocyclic groupshaving 1 to 4 rings. Illustrative examples include dimethylamino,diethylamino, dibutylamino, diphenylamino, ditolylamino, andbisbiphenylylamino groups.

[0081] Examples of the fused ring include indene, naphthalene,anthracene, phenanthrene, quinoline, isoquinoline, quinoxaline,phenazine, acridine, indole, carbazole, phenoxazine, phenothiazine,benzothiazole, benzothiophene, benzofuran, acridone, benzimidazole,coumarin, and flavone.

[0082] Of the naphthacene derivatives used herein, those of thefollowing formula (VII′) are preferred because devices are given alonger lifetime.

[0083] In formula (VII′), Q⁵¹ to Q⁵⁵ and Q²¹ to Q²⁵ are the same as Q¹¹in formula (VII).

[0084] Illustrative examples of the preferred naphthacene derivativesused herein are given below as IB-1 to IB-189. The substituents Q¹ to Q⁸are denoted as Q¹⁰ to Q⁸⁰. TABLE 1 SUBSTITUENT Compound No. Q¹⁰ Q²⁰ Q³⁰Q⁴⁰ Q⁵⁰ Q⁶⁰ Q⁷⁰ Q⁸⁰ IB-1

H H H H IB-2

H H H H IB-3

H H H H IB-4

H H H H IB-5

H H H H IB-6

H H H H IB-7

H H H H IB-8

H H H H

[0085] TABLE 2 SUBSTITUENT Compound No. Q¹⁰ Q²⁰ Q³⁰ Q⁴⁰ Q⁵⁰ Q⁶⁰ Q⁷⁰ Q⁸⁰IB-9 

H H H H IB-10

H H H H IB-11

H H H H IB-12

H H H H IB-13

H H H H IB-14

H H H H IB-15

H H H H IB-16

H H H H

[0086] TABLE 3 SUBSTITUENT Compound No. Q¹⁰ Q²⁰ Q³⁰ Q⁴⁰ Q⁵⁰ Q⁶⁰ Q⁷⁰ Q⁸⁰IB-17

H H H H IB-18

H H H H IB-19

H H H H IB-20

H H H H IB-21

H H H H IB-22

H H H H IB-23

H H H H IB-24

H H H H

[0087] TABLE 4 SUBSTITUENT Compound No. Q¹⁰ Q²⁰ Q³⁰ Q⁴⁰ Q⁵⁰ Q⁶⁰ Q⁷⁰ Q⁸⁰IB-25

H H H H IB-26

H H H H IB-27

H H H H IB-28

H H H H IB-29

H H H H IB-30

H H H H IB-31

H H H H IB-32

H H H H

[0088] TABLE 5 SUBSTITUENT Com- pound No. Q¹⁰ Q²⁰ Q³⁰ Q⁴⁰ Q⁵⁰ Q⁶⁰ Q⁷⁰Q⁸⁰ IB-33

H H H H IB-34

H H H H IB-35

H H H H IB-36

H H H H IB-37

H H H H IB-38

H H H H IB-39

H H H H IB-40

H H H H

[0089] TABLE 6 SUBSTITUENT Com- pound No. Q¹⁰ Q²⁰ Q³⁰ Q⁴⁰ Q⁵⁰ Q⁶⁰ Q⁷⁰Q⁸⁰ IB-41

H H H H IB-42

H H H H IB-43

H H H H IB-44

H H H H IB-45

H H H H IB-46

H H H H IB-47

H H H H

[0090] TABLE 7 SUBSTITUENT Compound No. Q¹⁰ Q²⁰ Q³⁰ Q⁴⁰ Q⁵⁰ Q⁶⁰ Q⁷⁰ Q⁸⁰IB-48

H H H H IB-49

H H H H IB-50

H H H H IB-51

H H H H IB-52

H H H H IB-53

H H H H IB-54

H H H H IB-55

H H H H

[0091] TABLE 8 SUBSTITUENT Compound No. Q¹⁰ Q²⁰ Q³⁰ Q⁴⁰ Q⁵⁰ Q⁶⁰ Q⁷⁰ Q⁸⁰IB-56

H H H H IB-57

H H H H IB-58

H H H H IB-59

H H H H IB-60

H H H H IB-61

H H H H IB-62

H H H H

[0092] TABLE 9 SUBSTITUENT Compound No. Q¹⁰ Q²⁰ Q³⁰ Q⁴⁰ Q⁵⁰ Q⁶⁰ Q⁷⁰ Q⁸⁰IB-63

H H H H IB-64

H H H H IB-65

H H H H IB-66

H H H H IB-67

H H H H IB-68

H H H H IB-69

H H H H

[0093] TABLE 10 SUBSTITUENT Com- pound No. Q¹⁰ Q²⁰ Q³⁰ Q⁴⁰ Q⁵⁰ Q⁶⁰ Q⁷⁰Q⁸⁰ IB-70

H H H H IB-71

H H H H IB-72

H H H H IB-73

H H H H IB-74

H H H H IB-75

H H H H IB-76

H H H H IB-77

H H H H

[0094] TABLE 11 SUBSTITUENT Compound No. Q¹⁰ Q²⁰ Q³⁰ Q⁴⁰ Q⁵⁰ Q⁶⁰ Q⁷⁰ Q⁸⁰IB-78

H H H H IB-79

H H H H IB-80

H H H H IB-81

H H H H IB-82

H H H H IB-83

H H H H IB-84

H H H H IB-85

H H H H

[0095] TABLE 12 SUBSTITUENT Compound No. Q¹⁰ Q²⁰ Q³⁰ Q⁴⁰ Q⁵⁰ Q⁶⁰ Q⁷⁰ Q⁸⁰IB-86

H H H H IB-87

H H H H IB-88

H H H H IB-89

H H H H IB-90

H H H H IB-91

H H H H IB-92

H H H H IB-93

H H H H

[0096] TABLE 13 SUBSTITUENT Compound No. Q¹⁰ Q²⁰ Q³⁰ Q⁴⁰ Q⁵⁰ Q⁶⁰ Q⁷⁰ Q⁸⁰IB-94

H H H H IB-95

H H H H IB-96

H H H H IB-97

H H H H IB-98

H H H H IB-99

H H H H IB-100

H H H H

[0097] TABLE 14 SUBSTITUENT Compound No. Q¹⁰ Q²⁰ Q³⁰ Q⁴⁰ Q⁵⁰ Q⁶⁰ Q⁷⁰ Q⁸⁰IB-101

H H H H IB-102

H H H H IB-103

H H H H IB-104

H H H H IB-105

H H H H IB-106

H H H H IB-107

H H H H IB-108

H H H H

[0098] TABLE 15 SUBSTITUENT Compound No. Q¹⁰ Q²⁰ Q³⁰ Q⁴⁰ Q⁵⁰ Q⁶⁰ Q⁷⁰ Q⁸⁰IB-109

H H H H IB-110

H H H H IB-111

H H H H IB-112

H H H H IB-113

H H H H IB-114

H H H H IB-115

H H H H IB-116

H H H H

[0099] TABLE 16 SUBSTITUENT Compound No. Q¹⁰ Q²⁰ Q³⁰ Q⁴⁰ Q⁵⁰ Q⁶⁰ Q⁷⁰ Q⁸⁰IB-117

H H H H IB-118

H H H H IB-119

H H H H IB-120

H H H H IB-121

H H H H IB-122

H H H H IB-123

H H H H IB-124

H H H H

[0100] TABLE 17 SUBSTITUENT Compound No. Q¹⁰ Q²⁰ Q³⁰ Q⁴⁰ Q⁵⁰ Q⁶⁰ Q⁷⁰ Q⁸⁰IB-125

H H H H IB-126

H H H H IB-127

H H H H IB-128

H H H H IB-129

H H H H IB-130

H H H H IB-131

H H H H IB-132

H H H H

[0101] TABLE 18 SUBSTITUENT Compound No. Q¹⁰ Q²⁰ Q³⁰ Q⁴⁰ Q⁵⁰ Q⁶⁰ Q⁷⁰ Q⁸⁰IB-133

H H H H IB-134

H H H H IB-135

H H H H IB-136

H H H H IB-137

H H H H IB-138

H H H H IB-139

H H H H IB-140

H H H H IB-141

H H H H

[0102] TABLE 19

SUBSTITUENT Compound No. Q¹⁰ Q²⁰ Q³⁰ Q⁴⁰ Q⁵⁰ Q⁶⁰ Q⁷⁰ Q⁸⁰ IB-142

H H IB-143

CH₃ CH₃ H H IB-144

IB-145

H H IB-146

H H IB-147

H H IB-148

CH₃ CH₃ CH₃ CH₃ IB-149

CH₃ CH₃ IB-150

IB-151

IB-152

[0103] TABLE 20

SUBSTITUENT Compound No. Q¹⁰ Q²⁰ Q³⁰ Q⁴⁰ Q⁵⁰ Q⁶⁰ Q⁷⁰ Q⁸⁰ IB-153

H H H H IB-154

H H IB-155

CH₃ CH₃ H H IB-156

IB-157

H H IB-158

H H IB-159

H H IB-160

CH₃ CH₃ CH₃ CH₃ IB-161

CH₃ CH₃

[0104] TABLE 21

SUBSTITUENT Com- pound No. Q¹⁰ Q²⁰ Q³⁰ Q⁴⁰ Q⁵⁰ Q⁶⁰ Q⁷⁰ Q⁸⁰ IB-162

CH₃ CH₃ H H IB-163

CH₃ CH₃ H H IB-164 CH₃

CH₃ H H H H IB-165 CH₃

CH₃ H H H H IB-166 CH₃

CH₃ H H H H IB-167 CH₃

CH₃ H H H H IB-168 H

H CH₃ CH₃ H H IB 169 H

H CH₃ CH₃ H H IB-170 H

H CH₃ CH₃ H H

[0105] TABLE 22

SUBSTITUENT Compound No. Q¹⁰ Q²⁰ Q³⁰ Q⁴⁰ Q⁵⁰ Q⁶⁰ Q⁷⁰ Q⁸⁰ IB-171 H

H CH₃ CH₃ H H IB-172 H

H CH₃ CH₃ CH₃ CH₃ IB-173 H

H CH₃ CH₃ CH₃ CH₃ IB-174 H

H CH₃ CH₃ CH₃ CH₃ IB-175 H

H CH₃ CH₃ CH₃ CH₃

[0106] TABLE 23 SUBSTITUENT Com- pound No. Q¹⁰ Q²⁰ Q³⁰ Q⁴⁰ Q⁵⁰ Q⁶⁰ Q⁷⁰Q⁸⁰ IB-176

CH₃ CH₃ H H IB-177

CH₃ CH₃ H H IB-178 CH₃

CH₃ H H H H IB-179 CH₃

CH₃ H H H H IB-180 CH₃

CH₃ H H H H IB-181 CH₃

CH₃ H H H H

[0107] TABLE 24 SUBSTITUENT Compound No. Q¹⁰ Q²⁰ Q³⁰ Q⁴⁰ Q⁵⁰ Q⁶⁰ Q⁷⁰ Q⁸⁰IB-182 H

H CH₃ CH₃ H H IB-183 H

H CH₃ CH₃ H H IB-184 H

H CH₃ CH₃ H H IB-185 H

H CH₃ CH₃ H H IB-186 H

H CH₃ CH₃ CH₃ CH₃ IB-187 H

H CH₃ CH₃ CH₃ CH₃ IB-188 H

H CH₃ CH₃ CH₃ CH₃ IB-189 H

H CH₃ CH₃ CH₃ CH₃

[0108] Other illustrative examples of the preferred naphthacenederivatives used herein are given below as IIB-1 to IIB-32 and IIIB-1 toIIIB-36. The substituents Q¹ to Q⁸ are denoted as Q¹⁰ to Q⁸⁰. TABLE 25SUBSTITUENT Com- pound No. Q¹⁰ Q²⁰ Q³⁰ Q⁴⁰ Q⁵⁰ Q⁶⁰ Q⁷⁰ Q⁸⁰ IIB-1

H H H H IIB-2

H H H H IIB-3

H H H H IIB-4

H H H H IIB-5

H H H H IIB-6

H H H H IIB-7

H H H H IIB-8

H H H H

[0109] TABLE 26 SUBSTITUENT Compound No. Q¹⁰ Q²⁰ Q³⁰ Q⁴⁰ Q⁵⁰ Q⁶⁰ Q⁷⁰ Q⁸⁰IIB-9

H H H H IIB-10

H H H H IIB-11

H H H H IIB-12

H H H H IIB-13

H H H H IIB-14

H H H H IIB-15

H H H H

[0110] TABLE 27 SUBSTITUENT Com- pound No. Q¹⁰ Q²⁰ Q³⁰ Q⁴⁰ Q⁵⁰ Q⁶⁰ Q⁷⁰Q⁸⁰ IIB-16

H H H H IIB-17

H H H H IIB-18

H H H H IIB-19

H H H H IIB-20

H H H H IIB-21

H H H H

[0111] TABLE 28 SUBSTITUENT Com- pound No. Q¹⁰ Q²⁰ Q³⁰ Q⁴⁰ Q⁵⁰ Q⁶⁰ Q⁷⁰Q⁸⁰ IIB-22

H H H H IIB-23

H H H H IIB-24

H H H H IIB-25

H H H H IIB-26

H H H H

[0112] TABLE 29 SUBSTITUENT Compound No. Q¹⁰ Q²⁰ Q³⁰ Q⁴⁰ Q⁵⁰ Q⁶⁰ Q⁷⁰ Q⁸⁰IIB-27

H H H H IIB-28

H H H H IIB-29

H H H H IIB-30

H H H H IIB-31

H H H H IIB-32

H H H H

[0113] TABLE 30 SUBSTITUENT Com- pound No. Q¹⁰ Q²⁰ Q³⁰ Q⁴⁰ Q⁵⁰ Q⁶⁰ Q⁷⁰Q⁸⁰ IIIB-1

H H H H IIIB-2

H H H H IIIB-3

H H H H IIIB-4

H H H H IIIB-5

H H H H IIIB-6

H H H H

[0114] TABLE 31 SUBSTITUENT Compound No. Q¹⁰ Q²⁰ Q³⁰ IIIB-7 

IIIB-8 

IIIB-9 

IIIB-10

IIIB-11

IIIB-12

SUBSTITUENT Compound No. Q⁴⁰ Q⁵⁰ Q⁶⁰ Q⁷⁰ Q⁸⁰ IIIB-7 

H H H H IIIB-8 

H H H H IIIB-9 

H H H H IIIB-10

H H H H IIIB-11

H H H H IIIB-12

H H H H

[0115] TABLE 32 SUBSTITUENT Compound No. Q¹⁰ Q²⁰ Q³⁰ IIIB-13

IIIB-14

IIIB-15

IIIB-16

IIIB-17

IIIB-18

SUBSTITUENT Compound No. Q⁴⁰ Q⁵⁰ Q⁶⁰ Q⁷⁰ Q⁸⁰ IIIB-13

H H H H IIIB-14

H H H H IIIB-15

H H H H IIIB-16

H H H H IIIB-17

H H H H IIIB-18

H H H H

[0116] TABLE 33 SUBSTITUENT Compound No. Q¹⁰ Q²⁰ Q³⁰ Q⁴⁰ IIIB-19

IIIB-20

IIIB-21

IIIB-22

IIIB-23

IIIB-24

SUBSTITUENT Compound No. Q⁵⁰ Q⁶⁰ Q⁷⁰ Q⁸⁰ IIIB-19 H H H H IIIB-20 H H H HIIIB-21 H H H H IIIB-22 H H H H IIIB-23 H H H H IIIB-24 H H H H

[0117] TABLE 34 SUBSTITUENT Compound No. Q¹⁰ Q²⁰ Q³⁰ Q⁴⁰ IIIB-25

IIIB-26

IIIB-27

IIIB-28

IIIB-29

IIIB-30

SUBSTITUENT Compound No. Q⁵⁰ Q⁶⁰ Q⁷⁰ Q⁸⁰ IIIB-25 H H H H IIIB-26 H H H HIIIB-27 H H H H IIIB-28 H H H H IIIB-29 H H H H IIIB-30 H H H H

[0118] TABLE 35 SUBSTITUENT Compound No. Q¹⁰ Q²⁰ Q³⁰ IIIB-31

IIIB-32

IIIB-33

IIIB-34

IIIB-35

IIIB-36

SUBSTITUENTS Compound No. Q⁴⁰ Q⁵⁰ Q⁶⁰ Q⁷⁰ Q⁸⁰ IIIB-31

H H H H IIIB-32

H H H H IIIB-33

H H H H IIIB-34

H H H H IIIB-35

H H H H IIIB-36

H H H H

[0119] Further illustrative examples of the preferred naphthacenederivatives used herein are given below as IVB-1 to IVB-206 and VB-1 toVB-142. The substituents Q¹ to Q⁸ are denoted as Q¹⁰ to Q⁸⁰. TABLE 36SUBSTITUENT Compound No. Q¹⁰ Q²⁰ Q³⁰ IVB-1 

IVB-2 

IVB-3 

IVB-4 

IVB-5 

IVB-6 

IVB-7 

IVB-8 

IVB-9 

IVB-10

IVB-11

SUBSTITUENT Compound No. Q⁴⁰ Q⁵⁰ Q⁶⁰ Q⁷⁰ Q⁸⁰ IVB-1 

CH₃ CH₃ H H IVB-2 

CH₃ CH₃ H H IVB-3 

CH₃ CH₃ H H IVB-4 

CH₃ CH₃ H H IVB-5 

CH₃ CH₃ H H IVB-6 

CH₃ CH₃ CH₃ CH₃ IVB-7 

CH₃ CH₃ CH₃ CH₃ IVB-8 

CH₃ CH₃ CH₃ CH₃ IVB-9 

CH₃ CH₃ CH₃ CH₃ IVB-10

CH₃ CH₃ CH₃ CH₃ IVB-11

CH₃ CH₃ CH₃ CH₃

[0120] TABLE 37 SUBSTITUENT Compound No. Q¹⁰ Q²⁰ Q³⁰ Q⁴⁰ Q⁵⁰ Q⁶⁰ IVB-12

CH₃ CH₃ IVB-13

CH₃ CH₃ IVB-14

CH₃ CH₃ IVB-15

CH₃ CH₃ IVB-16

IVB-17

IVB-18

IVB-19

SUBSTITUENT Compound No. Q⁷⁰ Q⁸⁰ IVB-12 CH₃ CH₃ IVB-13 CH₃ CH₃ IVB-14CH₃ CH₃ IVB-15 CH₃ CH₃ IVB-16

IVB-17

IVB-18

IVB-19

[0121] TABLE 38 SUBSTITUENT Compound No. Q¹⁰ Q²⁰ Q³⁰ Q⁴⁰ Q⁵⁰ IVB-20

IVB-21

IVB-22

IVB-23

IVB-24

IVB-25

IVB-26

IVB-27

IVB-28

IVB-29

IVB-30

IVB-31

IVB-32

SUBSTITUENT Compound No. Q⁶⁰ Q⁷⁰ Q⁸⁰ IVB-20

IVB-21

IVB-22

IVB-23

IVB-24

IVB-25

IVB-26

IVB-27

IVB-28

IVB-29

IVB-30

IVB-31

IVB-32

[0122] TABLE 39 SUBSTITUENT Compound No. Q¹⁰ Q²⁰ Q³⁰ IVB-33

IVB-34

IVB-35

IVB-36

IVB-37

IVB-38

IVB-39

IVB-40

IVB-41

IVB-42

IVB-43

IVB-44

IVB-45

SUBSTITUENT Compound No. Q⁴⁰ Q⁵⁰ Q⁶⁰ Q⁷⁰ Q⁸⁰ IVB-33

IVB-34

IVB-35

IVB-36

IVB-37

IVB-38

IVB-39

IVB-40

H H IVB-41

H H IVB-42

H H IVB-43

H H IVB-44

H H IVB-45

H H

[0123] TABLE 40 SUBSTITUENT Compound No. Q¹⁰ Q²⁰ Q³⁰ IVB-46

IVB-47

IVB-48

IVB-48

IVB-49

IVB-50

IVB-51

IVB-52

IVB-53

IVB-54

IVB-55

IVB-56

IVB-57

IVB-58

SUBSTITUENTS Compound No. Q⁴⁰ Q⁵⁰ Q⁶⁰ IVB-46

IVB-47

IVB-48

IVB-49

IVB-50

IVB-51

IVB-52

CH₃ CH₃ IVB-53

CH₃ CH₃ IVB-54

CH₃ CH₃ IVB-55

CH₃ CH₃ IVB-56

CH₃ CH₃ IVB-57

CH₃ CH₃ IVB-58

CH₃ CH₃ SUBSTITUENT Compound No. Q⁷⁰ Q⁸⁰ IVB-46 H H IVB-47 H H IVB-48 HH IVB-49 H H IVB-50 H H IVB-51 H H IVB-52 H H IVB-53 H H IVB-54 H HIVB-55 H H IVB-56 H H IVB-57 H H IVB-58 H H

[0124] TABLE 41 SUBSTITUENT Compound No. Q¹⁰ Q²⁰ Q³⁰ Q⁴⁰ Q⁵⁰ Q⁶⁰ Q⁷⁰ Q⁸⁰IVB-59

CH₃ CH₃ H H IVB-60

CH₃ CH₃ H H IVB-61

CH₃ CH₃ H H IVB-62

CH₃ CH₃ H H IVB-63

CH₃ CH₃ H H IVB-64

CH₃ CH₃ H H IVB-65

CH₃ CH₃ H H IVB-66

CH₃ CH₃ H H IVB-67

CH₃ CH₃ H H IVB-68

CH₃ CH₃ H H IVB-69

CH₃ CH₃ H H

[0125] TABLE 42 SUBSTITUENT Compound No. Q¹⁰ Q²⁰ Q³⁰ Q⁴⁰ Q⁵⁰ Q⁶⁰ Q⁷⁰ Q⁸⁰IVB-70

CH₃ CH₃ H H IVB-71

CH₃ CH₃ H H IVB-72

CH₃ CH₃ H H IVB-73

CH₃ CH₃ H H IVB-74

CH₃ CH₃ H H IVB-75

CH₃ CH₃ H H IVB-76

CH₃ CH₃ H H IVB-77

CH₃ CH₃ H H IVB-78

CH₃ CH₃ H H IVB-79

CH₃ CH₃ H H

[0126] TABLE 42 SUBSTITUENT Compound No. Q¹⁰ Q²⁰ Q³⁰ Q⁴⁰ Q⁵⁰ Q⁶⁰ Q⁷⁰ Q⁸⁰IVB-80

CH₃ CH₃ H H IVB-81

CH₃ CH₃ H H IVB-82

CH₃ CH₃ H H IVB-83

CH₃ CH₃ H H IVB-84

CH₃ CH₃ CH₃ CH₃ IVB-85

CH₃ CH₃ CH₃ CH₃ IVB-86

CH₃ CH₃ CH₃ CH₃ IVB-87

CH₃ CH₃ CH₃ CH₃

[0127] TABLE 44 SUBSTITUENT Compound No. Q¹⁰ Q²⁰ Q³⁰ Q⁴⁰ Q⁵⁰ Q⁶⁰ Q⁷⁰ Q⁸⁰IVB-88

CH₃ CH₃ CH₃ CH₃ IVB-89

CH₃ CH₃ CH₃ CH₃ IVB-90

CH₃ CH₃ CH₃ CH₃ IVB-91

CH₃ CH₃ CH₃ CH₃ IVB-92

CH₃ CH₃ CH₃ CH₃ IVB-93

CH₃ CH₃ CH₃ CH₃ IVB-94

CH₃ CH₃ CH₃ CH₃ IVB-95

CH₃ CH₃ CH₃ CH₃ IVB-96

CH₃ CH₃ CH₃ CH₃ IVB-97

CH₃ CH₃ CH₃ CH₃ IVB-98

CH₃ CH₃ CH₃ CH₃

[0128] TABLE 45 SUBSTITUENT Compound No. Q¹⁰ Q²⁰ Q³⁰ Q⁴⁰ Q⁵⁰ Q⁶⁰ Q⁷⁰ Q⁸⁰IVB-99 

CH₃ CH₃ CH₃ CH₃ IVB-100

CH₃ CH₃ CH₃ CH₃ IVB-101

CH₃ CH₃ CH₃ CH₃ IVB-102

CH₃ CH₃ CH₃ CH₃ IVB-103

CH₃ CH₃ CH₃ CH₃ IVB-104

CH₃ CH₃ CH₃ CH₃ IVB-105

CH₃ CH₃ CH₃ CH₃ IVB-106

CH₃ CH₃ CH₃ CH₃ IVB-107

CH₃ CH₃ CH₃ CH₃ IVB-108

CH₃ CH₃ CH₃ CH₃

[0129] TABLE 46 SUBSTITUENT Compound No. Q¹⁰ Q²⁰ Q³⁰ Q⁴⁰ Q⁵⁰ Q⁶⁰ Q⁷⁰ Q⁸⁰IVB-109

CH₃ CH₃ CH₃ CH₃ IVB-110

CH₃ CH₃ CH₃ CH₃ IVB-111

CH₃ CH₃ CH₃ CH₃ IVB-112

CH₃ CH₃ CH₃ CH₃ IVB-113

CH₃ CH₃ CH₃ CH₃ IVB-114

IVB-115

IVB-116

[0130] TABLE 47 SUBSTITUENT Compound No. Q¹⁰ Q²⁰ Q³⁰ Q⁴⁰ Q⁵⁰ Q⁶⁰ Q⁷⁰ Q⁸⁰IVB-117

IVB-118

IVB-119

IVB-120

IVB-121

IVB-122

IVB-123

IVB-124

IVB-125

[0131] TABLE 48 SUBSTITUENT Compound No. Q¹⁰ Q²⁰ Q³⁰ Q⁴⁰ Q⁵⁰ Q⁶⁰ Q⁷⁰ Q⁸⁰IVB-126

IVB-127

IVB-128

IVB-129

IVB-130

IVB-131

IVB-132

IVB-133

IVB-134

[0132] TABLE 49 SUBSTITUENT Compound No. Q¹⁰ Q²⁰ Q³⁰ Q⁴⁰ Q⁵⁰ Q⁶⁰ Q⁷⁰ Q⁸⁰IVB-135

IVB-136

IVB-137

IVB-138

IVB-139

IVB-140

IVB-141

[0133] TABLE 50 SUBSTITUENT Compound No. Q¹⁰ Q²⁰ Q³⁰ Q⁴⁰ Q⁵⁰ Q⁶⁰ Q⁷⁰ Q⁸⁰IVB-142

IVB-143

IVB-144

H H IVB-145

H H IVB-146

H H IVB-147

H H IVB-148

H H IVB-149

H H IVB-150

H H

[0134] TABLE 51 SUBSTITUENT Compound No. Q¹⁰ Q²⁰ Q³⁰ Q⁴⁰ Q⁵⁰ Q⁶⁰ Q⁷⁰ Q⁸⁰IVB-151

H H IVB-152

H H IVB-153

H H IVB-154

H H IVB-155

H H IVB-156

H H IVB-157

H H IVB-158

H H IVB-159

H H IVB-160

H H IVB-161

H H

[0135] TABLE 52 SUBSTITUENT Compound No. Q¹⁰ Q²⁰ Q³⁰ Q⁴⁰ Q⁵⁰ Q⁶⁰ Q⁷⁰ Q⁸⁰IVB-162

H H IVB-163

H H IVB-164

H H IVB-165

H H IVB-166

H H IVB-167

H H IVB-168

H H IVB-169

H H

[0136] TABLE 53 SUBSTITUENT Compound No. Q¹⁰ Q²⁰ Q³⁰ Q⁴⁰ Q⁵⁰ Q⁶⁰ Q⁷⁰ Q⁸⁰IVB-170

H H IVB-171

H H IVB-172

H H IVB-173

H H IVB-174

H H IVB-175

H H

[0137] TABLE 54 SUBSTITUTENT Compound No. Q¹⁰ Q²⁰ Q³⁰ Q⁴⁰ Q⁵⁰ Q⁶⁰ Q⁷⁰Q⁸⁰ IVB-176

H H IVB-177

H H IVB-178

H H IVB-179

H H IVB-180

H H IVB-181

H H IVB-182

H H IVB-183

H H IVB-184

H H IVB-185

H H

[0138] TABLE 55 SUBSTITUENT Compound No. Q¹⁰ Q²⁰ Q³⁰ Q⁴⁰ Q⁵⁰ Q⁶⁰ Q⁷⁰ Q⁸⁰IVB-186

H H IVB-187

H H IVB-188

H H IVB-189

H H IVB-190

IVB-191

IVB-192

IVB-193

IVB-194

[0139] TABLE 56 SUBSTITUENT Compound No. Q¹⁰ Q²⁰ Q³⁰ Q⁴⁰ Q⁵⁰ Q⁶⁰ Q⁷⁰ Q⁸⁰IVB-195

IVB-196

IVB-197

IVB-198

IVB-199

IVB-200

IVB-201

IVB-202

IVB-203

[0140] TABLE 57 SUBSTITUENT Compound No. Q¹⁰ Q²⁰ Q³⁰ Q⁴⁰ Q⁵⁰ Q⁷⁰ Q⁷⁰ Q⁸⁰IVB-204

IVB-205

IVB-206

[0141] TABLE 58 SUBSTITUENT Compound No. Q¹⁰ Q²⁰ Q³⁰ Q⁴⁰ Q⁵⁰ Q⁶⁰ Q⁷⁰ Q⁸⁰VB-1 H

H H H H H VB-2 H

H H H H H VB-3 H

H H H H H VB-4 H

H H H H H VB-5 H

H H H H H VB-6 H

H H H H H VB-7 H

H H H H H VB-8 H

H H H H H VB-9 H

H H H H H VB-10 H

H H H H H VB-11 H

H H H H H VB-12 H

H H H H H VB-13 H

H H H H H VB-14 H

H H H H H

[0142] TABLE 59 SUBSTITUENT Compound No. Q¹⁰ Q²⁰ Q³⁰ Q⁴⁰ Q⁵⁰ Q⁶⁰ Q⁷⁰ Q⁸⁰VB-15 H

H H H H H VB-16 H

H H H H H VB-17 H

H H H H H VB-18 H

H H H H H VB-19 H

H H H H H VB-20 H

H H H H H VB-21 H

H H H H H VB-22 H

H H H H H VB-23 H

H H H H H VB-24 H

H H H H H VB-25 H

H H H H H VB-26 H

H H H H H

[0143] TABLE 60 SUBSTITUENT Compound No. Q¹⁰ Q²⁰ Q³⁰ Q⁴⁰ Q⁵⁰ Q⁶⁰ Q⁷⁰ Q⁸⁰VB-27 H

H H H H H VB-28 H

H H H H H VB-29 H

H H H H H VB-30 H

H H H H H VB-31 H

H H H H H VB-32 H

H H H H H VB-33 H

H H H H H VB-34 H

H H H H H VB-35 H

H H H H H VB-36 H

H H H H H VB-37 H

H H H H H VB-38 H

H H H H H VB-39 H

H H H H H

[0144] TABLE 61 SUBSTITUENT Compound No. Q¹⁰ Q²⁰ Q³⁰ Q⁴⁰ Q⁵⁰ Q⁶⁰ Q⁷⁰ Q⁸⁰VB-40 H

H H H H H VB-41 H

H H H H H VB-42 H

H H H H H VB-43 H

H H H H H VB-44 H

H H H H H VB-45 H

H H H H H VB-46 H

H H H H H VB-47 H

H H H H H VB-48 H

H H H H H VB-49 H

H H H H H VB-50 H

H H H H H VB-51 H

H H H H H

[0145] TABLE 62 SUBSTITUENT Compound No. Q¹⁰ Q²⁰ Q³⁰ Q⁴⁰ Q⁵⁰ Q⁶⁰ Q⁷⁰ Q⁸⁰VB-52 H

H H H H H VB-53 H

H H H H H VB-54 H

H H H H H VB-55 H

H H H H H VB-56 H

H H H H H VB-57 H

H H H H H VB-58 H

H H H H H VB-59 H

H H H H H VB-60 H

H H H H H

[0146] TABLE 63 SUBSTITUENT Compound No. Q¹⁰ Q²⁰ Q³⁰ Q⁴⁰ Q⁵⁰ Q⁶⁰ Q⁷⁰ Q⁸⁰VB-61 H

H H H H H VB-62 H

H H H H H VB-63 H

H H H H H VB-64 H

H H H H H VB-65 H

H H H H H VB-66 H

H H H H H VB-67 H

H H H H H VB-68 H

H H H H H VB-69 H

H H H H H VB-70 H

H H H H H

[0147] TABLE 64 SUBSTITUENT Compound No. Q¹⁰ Q²⁰ Q³⁰ Q⁴⁰ Q⁵⁰ Q⁶⁰ Q⁷⁰ Q⁸⁰VB-71 H

H Ph Ph Ph Ph VB-72 H

H Ph Ph Ph Ph VB-73 H

H Ph Ph Ph Ph VB-74 H

H Ph Ph Ph Ph VB-75 H

H Ph Ph Ph Ph VB-76 H

H Ph Ph Ph Ph VB-77 H

H Ph Ph Ph Ph VB-78 H

H Ph Ph Ph Ph VB-79 H

H Ph Ph Ph Ph VB-80 H

H Ph Ph Ph Ph VB-81 H

H Ph Ph Ph Ph VB-82 H

H Ph Ph Ph Ph VB-83 H

H Ph Ph Ph Ph VB-84 H

H Ph Ph Ph Ph

[0148] TABLE 65 SUBSTITUENT Compound No. Q¹⁰ Q²⁰ Q³⁰ Q⁴⁰ Q⁵⁰ Q⁶⁰ Q⁷⁰ Q⁸⁰VB-85 H

H Ph Ph Ph Ph VB-86 H

H Ph Ph Ph Ph VB-87 H

H Ph Ph Ph Ph VB-88 H

H Ph Ph Ph Ph VB-89 H

H Ph Ph Ph Ph VB-90 H

H Ph Ph Ph Ph VB-91 H

H Ph Ph Ph Ph VB-92

H Ph Ph Ph Ph VB-93 H

H Ph Ph Ph Ph VB-94 H

H Ph Ph Ph Ph VB-95 H

H Ph Ph Ph Ph VB-96 H

H Ph Ph Ph Ph

[0149] TABLE 66 SUBSTITUENT Compound No. Q¹⁰ Q²⁰ Q³⁰ Q⁴⁰ Q⁵⁰ Q⁶⁰ Q⁷⁰ Q⁸⁰VB-97  H

H Ph Ph Ph Ph VB-98  H

H Ph Ph Ph Ph VB-99  H

H Ph Ph Ph Ph VB-100 H

H Ph Ph Ph Ph VB-101 H

H Ph Ph Ph Ph VB-102 H

H Ph Ph Ph Ph VB-103 H

H Ph Ph Ph Ph VB-104 H

H Ph Ph Ph Ph VB-105 H

H Ph Ph Ph Ph VB-106 H

H Ph Ph Ph Ph

[0150] TABLE 67 SUBSTITUENT Compound No. Q¹⁰ Q²⁰ Q³⁰ Q⁴⁰ Q⁵⁰ Q⁶⁰ Q⁷⁰ Q⁸⁰VB-107 H

H Ph Ph H H VB-108 H

H Ph Ph H H VB-109 H

H Ph Ph H H VB-110 H

H Ph Ph H H VB-111 H

H Ph Ph H H VB-112 H

H Ph Ph H H VB-113 H

H Ph Ph H H VB-114 H

H Ph Ph H H VB-115 H

H Ph Ph H H VB-116 H

H Ph Ph H H VB-117 H

H Ph Ph H H VB-118 H

H Ph Ph H H VB-119 H

H Ph Ph H H VB-120 H

H Ph Ph H H

[0151] TABLE 68 SUBSTITUENT Compound No. Q¹⁰ Q²⁰ Q³⁰ Q⁴⁰ Q⁵⁰ Q⁶⁰ Q⁷⁰ Q⁸⁰VB-121 H

H Ph Ph H H VB-122 H

H Ph Ph H H VB-123 H

H Ph Ph H H VB-124 H

H Ph Ph H H VB-125 H

H Ph Ph H H VB-126 H

H Ph Ph H H VB-127 H

H Ph Ph H H VB-128 H

H Ph Ph H H VB-129 H

H Ph Ph H H VB-130 H

H Ph Ph H H VB-131 H

H Ph Ph H H VB-132 H

H Ph Ph H H

[0152] TABLE 69 SUBSTITUENT Compound No. Q¹⁰ Q²⁰ Q³⁰ Q⁴⁰ Q⁵⁰ Q⁶⁰ Q⁷⁰ Q⁸⁰VB-133 H

H Ph Ph H H VB-134 H

H Ph Ph H H VB-135 H

H Ph Ph H H VB-136 H

H Ph Ph H H VB-137 H

H Ph Ph H H VB-138 H

H Ph Ph H H VB-139 H

H Ph Ph H H VB-140 H

H Ph Ph H H VB-141 H

H Ph Ph H H VB-142 H

H Ph Ph H H

[0153] The naphthacene derivatives used herein can be synthesized, forexample, using diphenyltetracene quinone and analogues. A typicalsynthesis scheme is shown below.

[0154] The naphthacene derivatives are used as the host material incombination with dopants.

[0155] Tetraaryldiamine Compounds

[0156] Another class of organic compounds useful as the host materialaccording to the invention are tetraaryldiamine derivatives of thefollowing formula (II).

[0157] In the device of the invention, the use of the tetraaryldiaminederivative, preferably as the host material, helps induce strong lightemission from the dopant while controlling the interaction with thedopant.

[0158] In an exemplary organic EL device which was fabricated using atetraaryldiamine derivative doped with adibenzo[f,f′]diindeno[1,2,3-cd:1′,2′,3′-lm]perylene derivative, aluminance of at least 300 cd/m² at maximum was obtained at a currentdensity of 10 mA/cm² and a drive voltage as low as about 6.5 V. Whenoperated at a current density of about 500 mA/cm², the deviceconsistently produced a luminance of greater than about 15,000 cd/m².When operated at a current density of about 50 mA/cm², the device markeda very long lifetime as demonstrated by a half-life time of more than300 hours at an initial luminance of at least 2400 cd/cm². Since thetetraaryldiamine derivative has hole transporting ability, a mixturethereof with another of the above-mentioned host materials enables tocontrol carrier balance, resulting in a device with a high efficiencyand long lifetime.

[0159] In organic EL devices as mentioned above, the dopantconcentration ensuring a chromatic purity and maximum efficiency isabout 1% by weight although dopant concentrations of about 2 or 3% byweight lead to devices which are practically acceptable albeit a drop ofless than about 10%.

[0160] In formula (II), R₁ to R₄ are independently aryl, fluorene,carbazolyl, alkyl, alkoxy, aryloxy, amino or halogen radicals, at leastone of R₁ to R₄ is aryl, and r1 to r4 each are 0 or an integer of 1 to5, with the proviso that r1 to r4 are not 0 at the same time, that is,r1+r2+r3+r4 is an integer of at least 1. R₅ and R₆ are independentlyalkyl, alkoxy, amino or halogen radicals and may be the same ordifferent, and r5 and r6 each are 0 or an integer of 1 to 4.

[0161] The aryl radicals represented by R₁ to R₄ may be monocyclic orpolycyclic, inclusive of fused rings and a collection of rings. Thosearyl radicals having 6 to 20 carbon atoms in total are preferred. Theymay have substituents, examples of which are alkyl, alkoxy, aryl,aryloxy, amino and halogen groups. Preferred examples of the arylradical represented by R₁ to R₄ include phenyl, o-, m- and p-tolyl,pyrenyl, naphthyl, anthryl, biphenylyl, phenylanthryl and tolylanthryl.Of these, phenyl is most preferred. Preferably the aryl radical,especially phenyl is bonded at the 3- or 4-position.

[0162] The alkyl radicals represented by R₁ to R₄ may be straight orbranched alkyl radicals, preferably of 1 to 10 carbon atoms. They mayhave substituents, examples of which are as illustrated for the arylradicals. Preferred examples of the alkyl radical represented by R₁ toR₄ include methyl, ethyl, n- and i-propyl, n-, i-, sec- and tert-butyl.

[0163] The alkoxy radicals represented by R₁ to R₄ are preferably thosehaving an alkyl moiety of 1 to 6 carbon atoms, for example, methoxy,ethoxy, and t-butoxy. The alkoxy radicals may have substituents.

[0164] Examples of the aryloxy radicals represented by R₁ to R₄ includephenoxy, 4-methylphenoxy, and 4-(t-butyl)phenoxy.

[0165] The amino radicals represented by R₁ to R₄ may be substituted orunsubstituted, with the substituted amino radicals being preferred.Illustrative examples include dimethylamino, diethylamino,diphenylamino, phenyltolylamino and bis(biphenyl)amino radicals.

[0166] Examples of the halogen atom represented by R₁ to R₄ are chlorineand bromine.

[0167] At least one of R₁ to R₄ is an aryl radical, and preferably atleast two, more preferably at least three of R₁ to R₄ are aryl radicals.It is then preferred that at least two, more preferably at least threeof r1 to r4 are integers of at least 1. Especially at least two, evenmore preferably at least three of r1 to r4 are equal to 1.

[0168] In formula (II), the alkyl, alkoxy, amino and halogen radicalsrepresented by R₅ and R₆ are the same as illustrated for R₁ to R₄.

[0169] It is preferred that both r5 and r6 be 0, that is, thebiphenylene radical connecting two arylamino radicals be anunsubstituted one.

[0170] When r1 to r4 are integers of at least 2, the R₁ groups, R₂groups, R₃ groups and R₄ groups may be identical or different,respectively. When r5 and r6 are integers of at least 2, the R₅ groupsand R₆ groups may be identical or different, respectively.

[0171] Of the compounds of formula (II), those compounds of thefollowing formulas (II-1) and (II-2) are preferred.

[0172] In formulas (II-1) and (II-2), R₇ to R₁₀ are independently alkyl,alkoxy, aryl, aryloxy, amino radicals or halogen atoms, and may be thesame or different. Illustrative examples are the same as described forR₁ to R₄ in formula (II). Letters r7 to r10 are each 0 or an integer of1 to 4. It is preferred that r7 to r10 be 0 in both formulas (II-1) and(II-2).

[0173] R₁₁ to R₁₄ are independently alkyl, alkoxy, aryl, aryloxy, aminoradicals or halogen atoms, and may be the same or different.Illustrative examples are the same as described for R₁ to R₄ in formula(II). Letters r11 to r14 are each 0 or an integer of 1 to 5.

[0174] R₅, R₆, r5 and r6 in formulas (II-1) and (II-2) are as defined informula (II). It is preferred that r5 and r6 be 0.

[0175] In formulas (II-1) and (II-2), when each of r7 to r10 is aninteger of at least 2, the R₇ groups, R₈ groups, R₉ groups and R₁₀groups may be the same or different, respectively; and when each of r11to r14 is an integer of at least 2, the R₁₁ groups, R₁₂ groups, R₁₃groups and R₁₄ groups may be the same or different, respectively.

[0176] Of the compounds of formula (II), those compounds of thefollowing formula (II-3) are also preferred.

[0177] R₅, R₆, r5 and r6 in formula (II-3) are as defined in formula(II). It is preferred that r5 and r6 be 0.

[0178] Ar₁ and Ar₂ each are an aryl radical and may be the same ordifferent. Illustrative examples of the aryl radical are as describedfor R₁ to R₄ in formula (II). Phenyl and biphenyl radicals are preferredamong others.

[0179] R₁₅ and R₁₆ are independently alkyl, alkoxy, aryl, aryloxy, aminoradicals or halogen atoms, and may be the same or different.Illustrative examples are the same as described for R₁ to R₄ in formula(II). Letters r15 and r16 are each 0 or an integer of 1 to 4. It ispreferred that r15 and r16 be 0.

[0180] R₁₇ and R₁₈ are independently alkyl, alkoxy, aryloxy, aminoradicals or halogen atoms, and may be the same or different.Illustrative examples are the same as described for R₁ to R₄ in formula(II). Letters r17 and r18 are each 0 or an integer of 1 to 5. It ispreferred that r17 and r18 be 0.

[0181] In formula (II-3), when each of r15 and r16 is an integer of atleast 2, the R₁₅ groups and R₁₆ groups may be the same or different,respectively; and when each of r17 and r18 is an integer of at least 2,the R₁₇ groups and R₁₈ groups may be the same or different,respectively.

[0182] Illustrative, non-limiting, examples of the compound of formula(II) are given below. It is noted that general formulas are followed bylists of R's to show illustrative examples by combinations of R's andoptionally Ar's. As to a set of R's, when all R's in that set arehydrogen, H is assigned to that set. When a substituent is present asany of R's in a set, only the substituent is designated in the set,indicating that the remainders are hydrogen. Ar₁ and Ar₂ areindividually shown.

Com- pound No. R¹˜R⁴ R⁵˜R⁹ R¹⁰˜R¹³ R¹⁴˜R¹⁸ R¹⁹˜R²² R²³˜R²⁷ R²⁸˜R³¹R³²˜R³⁶ R³⁷˜R⁴⁴ I-1 H H H H H H H H H I-2 H R⁶ = CH₃ H R¹⁷═CH₃ H R²⁶ =CH₃ H R³⁵ = CH₃ H I-3 H R⁷ = CH₃ H R¹⁶ = CH₃ H R²⁵ = CH₃ H R³⁴ = CH₃ HI-4 H R⁷ = t-C₄H₉ H R¹⁶ = t-C₄H₉ H R²⁵ = t-C₄H₉ H R³⁴ = t-C₄H₉ H I-5 HR⁷ = OCH₃ H R¹⁶ = OCH₃ H R²⁵ = OCH₃ H R³⁴ = OCH₃ H I-6 H R⁷ = Ph H R¹⁶ =Ph H R²⁵ = Ph H R³⁴ = Ph H I-7 H

H

H

H

H I-8 H R⁷ = OPh H R¹⁶ = OPh H R²⁵ = OPh H R³⁴ = OPh H I-9 H R⁷ =N(C₂H₅)₂ H R¹⁶ = N(C₂H₅)₂ H R²⁵ = N(C₂H₅)₂ H R³⁴ = N(C₂H₅)₂ H I-10 H R⁷= N(Ph)₂ H R¹⁶ = N(Ph)₂ H R²⁵ = N(Ph)₂ H R³⁴ = N(Ph)₂ H I-11 H R⁷ = Cl HR¹⁶ = Cl H R²⁵ = Cl H R³⁴ = Cl H I-12 R² = CH₃ H R¹¹ = CH₃ H R²⁰ = CH₃ HR²⁹ = CH₃ H H I-13 H R⁶ = Ph H R¹⁷ = Ph H R²⁶ = Ph H R³⁵ = Ph H I-14 HR⁷ = Ph H R¹⁶ = Ph H H H H H I-15 H R⁶ = Ph H R¹⁷ = Ph H H H H H I-16 R²= OCH₃ H R¹¹ = OCH₃ H R²⁰ = OCH₃ H R²⁹ = OCH₃ H H I-17 R² = Ph H R¹¹ =Ph H R²⁰ = Ph H R²⁹ = Ph H H I-18 R² = OPh H R¹¹ = OPh H R²⁰ = OPh H R²⁹= OPh H H I-19 R² = N(C₂H₅)₂ H R¹¹ = N(C₂H₅)₂ H R²⁰ = N(C₂H₅)₂ H R²⁹ =N(C₂H₅)₂ H H I-20 R² = Cl H R¹¹ = Cl H R²⁰ = Cl H R²⁹ = Cl H H I-21 H HH H H H H H R³⁷ = R⁴² = CH₃ I-22 H H H H H H H H R³⁷ = R⁴² = OCH₃ I-23 HH H H H H H H R³⁷ = R⁴² = N(C₂H₅)₂ I-24 H H H H H H H H R³⁷ = R⁴² = ClI-25 H H H H H H H H R⁴⁰ = R⁴³ = CH₃ I-26 R² = Ph R⁷ = Ph R¹¹ = Ph R¹⁶ =Ph R²⁰ = Ph R²⁵ = Ph R²⁹ = Ph R³⁴ = Ph H I-27 R² = N(Ph)₂ H R¹¹ = Ph HR²⁰ = Ph H R²⁹ = Ph H H I-28 H R⁶ = CH₃ H R¹⁶ = CH₃ H R²⁶ = CH₃ H R³⁴ =CH₃ H I-29 H R⁶ = R⁸ = CH₃ H H H R²⁴ = R²⁶ = CH₃ H H H

[0183]

Com- pound No. R⁵¹˜R⁵⁴ R⁵⁵˜R⁵⁹ R⁶⁰˜R⁶³ R⁶⁴˜R⁶⁸ R⁶⁹˜R⁷² R⁷³˜R⁷⁷ R⁷⁸˜R⁸¹R⁸²˜R⁸⁶ R⁸⁷˜R⁹⁴ II-1 H H H H H H H H H II-2 H R⁵⁶ = CH₃ H R⁶⁷ = CH₃ HR⁷⁴ = CH₃ H R⁸⁵ = CH₃ H II-3 H R⁵⁷ = CH₃ H R⁶⁶ = CH₃ H R⁷⁵ = CH₃ H R⁸⁴ =CH₃ H II-4 H R⁵⁷ = t-C₄H₉ H R⁶⁶ = t-C₄H₉ H R⁷⁵ = t-C₄H₉ H R⁸⁴ = t-C₄H₉ HII-5 H R⁵⁷ = OCH₃ H R⁶⁶ = OCH₃ H R⁷⁵ = OCH₃ H R⁸⁴ = OCH₃ H II-6 H R⁵⁷ =Ph H R⁶⁶ = Ph H R⁷⁵ = Ph H R⁸⁴ = Ph H II-7 H

H

H

H

H II-8 H R⁵⁷ = OPh H R⁶⁶ = OPh H R⁷⁵ = OPh H R⁸⁴ = OPh H II-9 H R⁵⁷ =N(C₂H₅)₂ H R⁶⁶ = N(C₂H₅)₂ H R⁷⁵ = N(C₂H₅)₂ H R⁸⁴ = N(C₂H₅)₂ H II-10 HR⁵⁷ = N(Ph)₂ H R⁶⁶ = N(Ph)₂ H R⁷⁵ = N(Ph)₂ H R⁸⁴ = N(Ph)₂ H II-11 H R⁵⁷= Cl H R⁶⁶ = Cl H R⁷⁵ = Cl H R⁸⁴ = Cl H II-12 R⁵² = CH₃ H R⁶² = CH₃ HR⁷² = CH₃ H R⁷⁹ = CH₃ H H II-13 R⁵² = OCH₃ H R⁶² = OCH₃ H R⁷² = OCH₃ HR⁷⁹ = OCH₃ H H II-14 R⁵² = Ph H R⁶² = Ph H R⁷² = Ph H R⁷⁹ = Ph H H II-15R⁵² = OPh H R⁶² = OPh H R⁷² = OPh H R⁷⁹ = OPh H H II-16 R⁵² = N(C₂H₅)₂ HR⁶² = N(C₂H₅)₂ H R⁷² = N(C₂H₅)₂ H R⁷⁹ = N(C₂H₅)₂ H H II-17 R⁵² = Cl HR⁶² = Cl H R⁷² = Cl H R⁷⁹ = Cl H H II-18 H H H H H H H H R⁸⁷ = R⁹² = CH₃II-19 H H H H H H H H R⁸⁷ = R⁹² = OCH₃ II-20 H H H H H H H H R⁸⁷ = R⁹² =N(C₂H₅)₂ II-21 H H H H H H H H R⁸⁷ = R⁹² = Cl II-22 H H H H H H H H R⁹⁰= R⁹² = CH₃ II-23 H R⁵⁷ = CH₃ H R⁶⁷ = CH₃ H R⁷⁵ = CH₃ H R⁸⁵ = CH₃ HII-24 H R⁵⁶ = R⁵⁸ = CH₃ H H H R⁷⁴ = R⁷⁶ = CH₃ H H H

[0184]

Com- pound No. Ar₁ Ar₂ R¹⁰¹˜R¹⁰⁴ R¹⁰⁵˜R¹⁰⁸ R¹⁰⁹˜R¹¹³ R¹¹⁴˜R¹¹⁸ R¹¹⁹˜R¹²⁶III-1 Ph Ph H H H H H III-2 Ph Ph H H R¹¹⁰ = CH₃ R¹¹⁵ = CH₃ H III-3 PhPh H H R¹¹¹ = CH₃ R¹¹⁶ = CH₃ H III-4 Ph Ph H H R¹¹¹ = t-C₄H₉ R¹¹⁶ =t-C₄H₉ H III-5 Ph Ph H H R¹¹¹ = OCH₃ R¹¹⁶ = OCH₃ H III-6 Ph Ph H H R¹¹¹= Ph R¹¹⁶ = Ph H III-7 Ph Ph H H

H III-8 Ph Ph H H R¹¹¹ = OPh R¹¹⁶ = OPh H III-9 Ph Ph H H R¹¹¹ =N(C₂H₅)₂ R¹¹⁶ = N(C₂H₅)₂ H III-10 Ph Ph H H R¹¹¹ = N(Ph)₂ R¹¹⁶ = N(Ph)₂H III-11 Ph Ph H H R¹¹¹ = Cl R¹¹⁶ = Cl H III-12 Ph Ph R¹⁰² = CH₃ R¹⁰⁶ =CH₃ H H H III-13 Ph Ph H H R¹¹¹ = CH₃ R¹¹⁵ = CH₃ H III-14 Ph Ph H H R¹¹¹= OCH₃ R¹¹⁵ = OCH₃ H III-15 Ph Ph R¹⁰² = OCH₃ R¹⁰⁶ = OCH₃ H H H III-16Ph Ph R¹⁰² = Ph R¹⁰⁶ = Ph H H H III-17 Ph Ph R¹⁰² = OPh R¹⁰⁶ = OPh H H HIII-18 Ph Ph R¹⁰² = N(C₂H₅)₂ R¹⁰⁶ = N(C₂H₅)₂ H H H III-19 Ph Ph R¹⁰² =Cl R¹⁰⁶ = Cl H H H III-20 Ph Ph H H H H R¹¹⁹ = R¹²⁴ = CH₃ III-21 Ph Ph HH H H R¹¹⁹ = R¹²⁴ = OCH₃ III-22 Ph Ph H H H H R¹¹⁹ = R¹²⁴ = N(C₂H₅)₂III-23 Ph Ph H H H H R¹¹⁹ = R¹²⁴ = Cl III-24

H H H H H III-25

H H H H H III-26

H H H H H III-27 Ph

H H H H H III-28

H H H H H

[0185] IV-1

IV-2

IV-3

IV-4

IV-5

V-1

V-2

V-3

V-4

V-5

VI-1

VI-2

VI-3

VI-4

R₃ = R₂₃ R₄ = R₂₄ R₁₃ = R₃₃ R₁₄ = R₄₄ Ph H H H H Ph H H Ph H Ph H H Ph HPh CH₃ H H H H CH₃ H H CH₃ H CH₃ H H CH₃ H CH₃

[0186] The above-described host compounds can be synthesized by themethod described in Jean Piccard, Herr. Chim. Acta., 7, 789 (1924), JeanPiccard, J. Am. Chem. Soc., 48, 2878 (1926), etc. or similar methods.More particularly, Ullmann reaction is effected by heating in thepresence of copper a combination of a di(biphenyl)amine compound with adiiodobiphenyl compound or a combination of a N,N′-diphenylbenzidinecompound with a iodobiphenyl compound, selected in accordance with theend compound.

[0187] The host compounds can be identified by mass analysis, infrared(IR) absorption spectroscopy or nuclear magnetic resonance spectroscopy(¹H-NMR).

[0188] These compounds have a molecular weight of about 640 to about800, a high melting point of about 190 to about 300° C., and a highglass transition temperature of about 80 to about 150° C. Onconventional vacuum evaporation, they form satisfactory smooth filmswhich are transparent and remain amorphous even above room temperature.The films maintain the stable amorphous state over a long period oftime. Accordingly, thin films can be formed from the compounds alonewithout a need for binder resins.

[0189] Anthracene Compounds

[0190] A further class of organic compounds useful as the host materialaccording to the invention are phenylanthracene derivatives of thefollowing formula (III).

[0191] In the device of the invention, the use of the anthracenederivative of formula (III), preferably as the host material, helpsinduce strong light emission from the dopant while controlling theinteraction with the dopant. Since the anthracene derivatives are fullyheat resistant and durable, organic EL devices with a longer lifetimeare obtainable.

[0192] In an exemplary organic EL device which was fabricated using ananthracene derivative doped with adibenzo[f,f′]diindeno[1,2,3-cd:1′,2′,3′-lm]perylene derivative, aluminance of at least 250 cd/m² was obtained at a current density of 10mA/cm² and a drive voltage as low as about 6.5 V. When operated at acurrent density of about 600 mA/cm², the device consistently produced aluminance of greater than about 13,000 cd/m². When operated at a currentdensity of about 50 mA/cm², the device marked a very long lifetime asdemonstrated by a half-life time of more than 300 hours at an initialluminance of at least 2400 cd/cm².

[0193] In organic EL devices as mentioned above, the dopantconcentration ensuring a chromatic purity and maximum efficiency isabout 1% by weight although dopant concentrations of about 2 or 3% byweight lead to devices which are practically acceptable albeit a drop ofless than about 10%.

[0194] Herein A₁₀₁ is a monophenylanthryl or diphenylanthryl radical andmay be the same or different, L is hydrogen, a single bond or a divalentlinkage, and n is an integer of 1 or 2.

[0195] Of the compounds of formula (III), those compounds of thefollowing formulas (III-1) and (III-2) are preferred.

[0196] Evaporated films of these compounds remain in a stable amorphousstate, that is, have sufficient physical properties to produceconsistent uniform light emission. The films remain stable over one yearin the ambient atmosphere without crystallization.

[0197] Referring to formula (III), A₁₀₁ is a monophenylanthryl ordiphenylanthryl radical and may be the same or different, and n is aninteger of 1 or 2. The monophenylanthryl or diphenylanthryl radicalrepresented by A₁₀₁ may be substituted or unsubstituted. Exemplarysubstituents are alkyl, aryl, alkoxy, aryloxy and amino groups. Thesesubstituents may further have substituents thereon and will be describedlater. The position of a substituent on the monophenylanthryl ordiphenylanthryl radical is not critical although the preferredsubstitution position is on the phenyl group bonded to the anthracenering rather than the anthracene ring.

[0198] Preferably the phenyl group is bonded to the anthracene ring atthe 9- and 10-positions.

[0199] In formula (III), L is hydrogen, a single bond or a divalentlinkage. The divalent linkage represented by L is preferably an aryleneradical which may be separated by an alkylene or analogous group. Thearylene radical will be described later.

[0200] Of the phenylanthracene derivatives of formula (III), those offormulas (III-1) and (III-2) are preferred. Formula (III-1) is describedin detail.

[0201] In formula (III-1), M₁ and M₂ each are alkyl, cycloalkyl, aryl,alkoxy, aryloxy, amino or heterocyclic radicals.

[0202] The alkyl radicals represented by M₁ and M₂ may be substituted orunsubstituted, straight or branched alkyl radicals, preferably of 1 to10 carbon atoms, more preferably 1 to 4 carbon atoms. Unsubstitutedalkyl radicals of 1 to 4 carbon atoms are preferred, such as, forexample, methyl, ethyl, n- and i-propyl, and n-, i-, sec- andtert-butyl.

[0203] Exemplary of the cycloalkyl radicals represented by M₁ and M₂ arecyclohexyl and cyclopentyl.

[0204] The aryl radicals represented by M₁ and M₂ are preferably thosearyl radicals having 6 to 20 carbon atoms which may have substituentssuch as phenyl and tolyl. Preferred examples of the aryl radical includephenyl, o-, m- and p-tolyl, pyrenyl, naphthyl, anthryl, biphenyl,phenylanthryl and tolylanthryl.

[0205] The alkenyl radicals represented by M₁ and M₂ are preferablythose having 6 to 50 carbon atoms in total, which may be substituted orunsubstituted, with the substituted ones being preferred. Suchsubstituents are aryl groups such as phenyl. Exemplary alkenyl radicalsare triphenylvinyl, tritolylvinyl and tribiphenylvinyl.

[0206] The alkoxy radicals represented by M₁ and M₂ are preferably thosehaving an alkyl moiety of 1 to 6 carbon atoms, for example, methoxy andethoxy. The alkoxy radicals may have substituents.

[0207] Exemplary of the aryloxy radicals represented by M₁ and M₂ isphenoxy.

[0208] The amino radicals represented by M₁ and M₂ may be substituted orunsubstituted, with the substituted amino radicals being preferred. Suchsubstituents are alkyl groups such as methyl and ethyl and aryl groupssuch as phenyl. Illustrative examples of the amino radical includediethylamino, diphenylamino and di(m-tolyl)amino radicals.

[0209] The heterocyclic radicals represented by M₁ and M₂ includebipyridyl, pyrimidyl, quinolyl, pyridyl, thienyl, furyl and oxadiazoylradicals and may have substituents such as methyl and phenyl.

[0210] In formula (III-1), q1 and q2 each are 0 or an integer of 1 to 5,especially 0 or 1. When q1 and q2 each are an integer of 1 to 5,especially 1 or 2, M₁ and M₂ each are preferably alkyl, aryl, alkenyl,alkoxy, aryloxy or amino radicals.

[0211] In formula (III-1), M₁ and M₂ may be the same or different. Wherea plurality of M₁ or M₂ are included, the M₁ groups or M₂ groups may bethe same or different. Alternatively, the M₁ groups or M₂ groups bondtogether to form a ring such as a benzene ring. The ring formation isalso a preferred embodiment.

[0212] In formula (III-1), L₁ is hydrogen, a single bond or an aryleneradical. The arylene radicals represented by L₁ are preferablyunsubstituted ones, for example, ordinary arylene radicals such asphenylene, biphenylene and anthrylene as well as two or more aryleneradicals which are directly bonded. L₁ is preferably a single bond,p-phenylene or 4,4′-biphenylene.

[0213] The arylene radical represented by L₁ may consist of two or morearylene radicals which are connected by an alkylene radical, —O—, —S— or—NR— wherein R is an alkyl or aryl radical. Exemplary alkyl radicals aremethyl and ethyl, and an exemplary aryl radical is phenyl. R ispreferably an aryl radical, such as phenyl. Alternatively, R is A₁₀₁ ora phenyl radical having A₁₀₁ substituted thereon. The alkylene radicalsare preferably methylene and ethylene.

[0214] Illustrative examples of the arylene radical are given below.

[0215] Next referring to formula (III-2), M₃ and M₄ are the same as M₁and M₂ in formula (III-1), q3 and q4 are the same as q1 and q2 informula (III-1), and L₂ is the same as L₁ in formula (III-1). Preferredexamples of these radicals are also the same.

[0216] In formula (III-2), M₃ and M₄ may be the same or different. Wherea plurality of M₃ or M₄ are included, the M₃ groups or M₄ groups may bethe same or different. Alternatively, the M₃ groups or M₄ groups bondtogether to form a ring such as a benzene ring. The ring formation isalso a preferred embodiment.

[0217] Illustrative, non-limiting, examples of the compounds of formulas(III-1) and (III-2) are given below. It is noted that general formulasare followed by lists of M's to show illustrative examples bycombinations of M₁₁ to M₁₅ and M₂₁ to M₂₅ or combinations of M₃₁ to M₃₅and M₄₁ to M₄₅.

Compound No. M₁₁ M₁₂ M₁₃ M₁₄ M₁₅ M₂₁ M₂₂ M₂₃ M₂₄ M₂₅ I-1  H H H H H H HH H H I-2  CH₃ H H H H CH₃ H H H H I-3  t-C₄H₉ H H H H t-C₄H₉ H H H HI-4  OCH₃ H H H H OCH₃ H H H H I-5  OPh H H H H OPh H H H H I-6 N(C₂H₅)₂ H H H H N(C₂H₅)₂ H H H H I-7  N(Ph)₂ H H H H N(Ph)₂ H H H HI-8  Ph H H H H Ph H H H H I-9 

H H H H

H H H H I-10 H CH₃ H H H H CH₃ H H H I-11 H CH₃ H CH₃ H H CH₃ H CH₃ HI-12 H H CH₃ H H H H CH₃ H H I-13 H CH₃ H H CH₃ H CH₃ H H CH₃ I-14t-C₄H₉ H H H H H H H H H I-15

H H H H

H H H H I-16 H Ph H H H H Ph H H H I-17 H H Ph H H H H Ph H H I-18

H H H H

H H H H I-19 n-C₄H₉ H H H H n-C₄H₉ H H H H I-20

H H H H

H H H H I-21 H H

H H H H

H H I-22

H H H H

H H H H I-23 H H

H H H H

H H I-24 H H Ph H Ph H H Ph H Ph I-25 H H Ph Ph H H H Ph Ph H

[0218]

Compound No. M₁₁ M₁₂ M₁₃ M₁₄ M₁₅ M₂₁ M₂₂ M₂₃ M₂₄ M₂₅ II-1  H H H H H H HH H H II-2  CH₃ H H H H CH₃ H H H H II-3  t-C₄H₉ H H H H t-C₄H₉ H H H HII-4  OCH₃ H H H H OCH₃ H H H H II-5  OPh H H H H OPh H H H H II-6 N(C₂H₅)₂ H H H H N(C₂H₅)₂ H H H H II-7  N(Ph)₂ H H H H N(Ph)₂ H H H HII-8  Ph H H H H Ph H H H H II-9 

H H H H

H H H H II-10 H CH₃ H H H H CH₃ H H H II-11 H H CH₃ H H H CH₃ CH₃ H HII-12 H H CH₃ CH₃ H H H CH₃ CH₃ H II-13 H H CH₃ H CH₃ H CH₃ CH₃ H CH₃II-14 CH₃ CH₃ CH₃ CH₃ CH₃ CH₃ CH₃ CH₃ CH₃ CH₃ II-15 t-C₄H₉ H H H H H H HH H II-16

H H H H

H H H H II-17 H Ph H H H H Ph H H H II-18 H H Ph H H H H Ph H H II-19 HH

H H H H

H H II-20

H H H H

H H H H II-21

H H H H

H H H H II-22 H H

H H H H

H H II-23 H H Ph H Ph H H Ph H Ph II-24 H H Ph Ph H H H Ph Ph H

[0219]

Compound No. M₁₁ M₁₂ M₁₃ M₁₄ M₁₅ M₂₁ M₂₂ M₂₃ M₂₄ M₂₅ III-1  H H H H H HH H H H III-2  CH₃ H H H H CH₃ H H H H III-3  t-C₄H₉ H H H H t-C₄H₉ H HH H III-4  OCH₃ H H H H OCH₃ H H H H III-5  OPh H H H H OPh H H H HIII-6  N(C₂H₅)₂ H H H H N(C₂H₅)₂ H H H H III-7  N(Ph)₂ H H H H N(Ph)₂ HH H H III-8  Ph H H H H Ph H H H H III-9 

H H H H

H H H H III-10 H CH₃ H H H H CH₃ H H H III-11 H H CH₃ H H H H CH₃ H HIII-12 H H CH₃ CH₃ H H H CH₃ CH₃ H III-13 H H CH₃ H CH₃ H H CH₃ H CH₃III-14 CH₃ CH₃ CH₃ CH₃ CH₃ CH₃ CH₃ CH₃ CH₃ CH₃ III-15 H Ph H H H H Ph HH H III-16 H H Ph H H H H Ph H H III-17

H H H H

H H H H III-18 t-C₄H₉ H H H H H H H H H III-19

H H H H

H H H H III-20

H H H H

H H H H III-21

H H H H

H H H H III-22

H H H H

H H H H III-23

H H H H

H H H H III-24 H H

H H H H

H H III-25

H H H H

H H H H III-26 H H

H H H H

H H III-27 H H Ph H Ph H H Ph H Ph III-28 H H Ph Ph H H H Ph Ph H

[0220]

Compound No. M₁₁ M₁₂ M₁₃ M₁₄ M₁₅ M₂₁ M₂₂ M₂₃ M₂₄ M₂₅ IV-1  H H H H H H HH H H IV-2  CH₃ H H H H CH₃ H H H H IV-3  t-C₄H₉ H H H H t-C₄H₉ H H H HIV-4  OCH₃ H H H H OCH₃ H H H H IV-5  OPh H H H H OPh H H H H IV-6 N(C₂H₅)₂ H H H H N(C₂H₅)₂ H H H H IV-7  N(Ph)₂ H H H H N(Ph)₂ H H H HIV-8  Ph H H H H Ph H H H H IV-9 

H H H H

H H H H IV-10 H CH₃ H H H H CH₃ H H H IV-11 H H CH₃ H H H H CH₃ H HIV-12 H H CH₃ CH₃ H H H CH₃ CH₃ H IV-13 H H CH₃ H CH₃ H H CH₃ H CH₃IV-14 CH₃ CH₃ CH₃ CH₃ CH₃ CH₃ CH₃ CH₃ CH₃ CH₃ IV-15 H H H H H H H H H HIV-16 H H Ph H H H H Ph H H IV-17

H H H H

H H H H IV-18 t-C₄H₉ H H H H H H H H H IV-19

H H H H

H H H H IV-20

H H H H

H H H H IV-21

H H H H

H H H H IV-22 H H

H H H H

H H IV-23

H H H H

H H H H IV-24 H H

H H H H

H H IV-25 H H Ph H Ph H H Ph H Ph IV-26 H H Ph Ph H H H Ph Ph H

[0221]

Compound No. M₃₁ M₃₂ M₃₃ M₃₄ M₃₅ M₄₁ M₄₂ M₄₃ M₄₄ M₄₅ V-1  H H H H H H HH H H V-2  CH₃ H H H H CH₃ H H H H V-3  t-C₄H₉ H H H H t-C₄H₉ H H H HV-4  OCH₃ H H H H OCH₃ H H H H V-5  OPh H H H H OPh H H H H V-6 N(C₂H₅)₂ H H H H N(C₂H₅)₂ H H H H V-7  N(Ph)₂ H H H H N(Ph)₂ H H H HV-8  Ph H H H H Ph H H H H V-9 

H H H H

H H H H V-10 H CH₃ H H H H CH₃ H H H V-11 H H CH₃ H H H H CH₃ H H V-12 HH CH₃ CH₃ H H H CH₃ CH₃ H V-13 H H CH₃ H CH₃ H H CH₃ H CH₃ V-14 CH₃ CH₃CH₃ CH₃ CH₃ CH₃ CH₃ CH₃ CH₃ CH₃ V-15 H Ph H H H H Ph H H H V-16 H H Ph HH H H Ph H H V-17

H H H H

H H H H V-18 t-C₄H₉ H H H H t-C₄H₉ H H H H V-19

H H H H

H H H H V-20

H H H H

H H H H V-21

H H H H

H H H H V-22

H H H H

H H H H V-23

H H H H

H H H H V-24

H H H H

H H H H V-25 H H

H H H H

H H V-26

H H H H

H H H H V-27 H H

H H H H

H H V-28 H H Ph H Ph H H Ph H Ph V-29 H H Ph Ph H H H Ph Ph H

[0222]

Compound No. M₃₁ M₃₂ M₃₃ M₃₄ M₃₅ M₄₁ M₄₂ M₄₃ M₄₄ M₄₅ VI-1  H H H H H H HH H H VI-2  CH₃ H H H H CH₃ H H H H VI-3  t-C₄H₉ H H H H t-C₄H₉ H H H HVI-4  OCH₃ H H H H OCH₃ H H H H VI-5  OPh H H H H OPh H H H H VI-6 N(C₂H₅)₂ H H H H N(C₂H₅)₂ H H H H VI-7  N(Ph)₂ H H H H N(Ph)₂ H H H HVI-8  Ph H H H H Ph H H H H VI-9 

H H H H

H H H H VI-10 H CH₃ H H H H CH₃ H H H VI-11 H H CH₃ H H H H CH₃ H HVI-12 H H CH₃ CH₃ H H H CH₃ CH₃ H VI-13 H H CH₃ H CH₃ H H CH₃ H CH₃VI-14 CH₃ CH₃ CH₃ CH₃ CH₃ CH₃ CH₃ CH₃ CH₃ CH₃ VI-15 H Ph H H H H Ph H HH VI-16 H H Ph H H H H Ph H H VI-17

H H H H

H H H H VI-18 t-C₄H₉ H H H H H H H H H VI-19

H H H H

H H H H VI-20

H H H H

H H H H VI-21

H H H H H H H H H VI-22

H H H H CH₃ H H H H VI-23

H H H H

H H H H VI-24

H H H H

H H H H VI-25 H H Ph H Ph H H Ph H Ph VI-26 H H Ph Ph H H H Ph Ph HVI-27 H H

H H H H

H H VI-28 H H

H H H H

H H

[0223]

Compound No. M₃₁ M₃₂ M₃₃ M₃₄ M₃₅ M₄₁ M₄₂ M₄₃ M₄₄ M₄₅ VII-1  H H H H H HH H H H VII-2  CH₃ H H H H CH₃ H H H H VII-3  t-C₄H₉ H H H H t-C₄H₉ H HH H VII-4  OCH₃ H H H H OCH₃ H H H H VII-5  OPh H H H H OPh H H H HVII-6  N(C₂H₅)₂ H H H H N(C₂H₅)₂ H H H H VII-7  N(Ph)₂ H H H H N(Ph)₂ HH H H VII-8  Ph H H H H Ph H H H H VII-9 

H H H H

H H H H VII-10 H H CH₃ CH₃ H H H CH₃ CH₃ H VII-11 H H CH₃ H CH₃ H H CH₃H CH₃ VII-12 H CH₃ H H H H CH₃ H H H VII-13 H H CH₃ H H H H CH₃ H HVII-14 CH₃ CH₃ CH₃ CH₃ CH₃ CH₃ CH₃ CH₃ CH₃ CH₃ VII-15 H H Ph H Ph H H PhH Ph VII-16 H H Ph Ph H H H Ph Ph H VII-17 H H

H H H H

H H VII-18 H H

H H H H

H H VII-19 H Ph H H H H Ph H H H VII-20 H H Ph H H H H Ph H H VII-21

H H H H

H H H H VII-22 t-C₄H₉ H H H H H H H H H VII-23

H H H H

H H H H VII-24

H H H H

H H H H VII-25

H H H H

H H H H VII-26

H H H H

H H H H VII-27

H H H H

H H H H VII-28 n-C₄H₉ H H H H n-C₄H₉ H H H H VII-29 H H OCH₃ H H H HOCH₃ H H VII-30 H R₃₂ and R₃₃ H H H R₃₂ and R₃₃ H H form a fused form afused benzene ring. benzene ring. VII-31

H H H H

H H H H VII-32

H H H H

H H H H VII-33 H H

H H H H

H H VII-34

H H H H

H H H H VII-35 H H

H H H H

H H VII-36 H H Ph H Ph H H Ph H Ph VII-37 H H Ph Ph H H H Ph Ph H

[0224]

Compound No. M¹¹═M²¹ M¹²═M²² M¹³═M²³ M¹⁴═M²⁴ M¹⁵═M²⁵ VIII′-1 H H H H HVIII′-2 CH₃ H H H H VIII′-3 H CH₃ H H H VIII′-4 H H CH₃ H H VIII′-5 Ph HCH₃ CH₃ H VIII′-6 H Ph H H H VIII′-7 H H Ph H H VIII′-8 H H Ph Ph HVIII′-9 H H Ph H Ph VIII′-10 H H

H H VIII′-11

H H H H VIII′-12 H H

H H VIII′-13

H H H H VIII′-14 N(Ph)₂ H H H H VIII′-15 N(C₂H₅)₂ H H H H VIII′-16 OCH₃H H H H VIII′-17 Oph H H H H VIII′-18

H H H H VIII′-19

H H H H

[0225]

[0226] The phenylanthracene derivatives used herein can be prepared bycoupling a halogenated diphenylanthracene compound with Ni(cod)₂ whereincod represents 1,5-cyclooctadiene, or cross-coupling a Grignard reagentof a dihalogenated aryl with a nickel complex such as NiCl₂(dppe) orNiCl₂(dppp) wherein dppe represents diphenylphosphinoethane and dppprepresents diphenylphosphinopropane. Alternatively, the phenylanthracenederivatives are prepared by a cross-coupling process involving reactinganthraquinone, benzoquinone, phenylanthrone or bianthrone with aGrignard reagent of aryl or a lithiated aryl followed by reduction.

[0227] These compounds can be identified by elemental analysis, massanalysis, IR spectroscopy, ¹H and ¹³C NMR, etc.

[0228] In general, the phenylanthracene derivatives have a molecularweight of about 400 to about 2,000, preferably about 400 to about 1,000,a high melting point of about 200 to about 500° C., and a high glasstransition temperature (Tg) of about 80 to about 250° C., preferablyabout 100 to 250° C., more preferably about 130 to 250° C., especiallyabout 150 to 250° C. By conventional vacuum deposition or the like, theyform a transparent, smooth film of quality which maintains a stableamorphous state even above room temperature and over a long period oftime.

[0229] Since the phenylanthracene derivatives are relatively neutralcompounds, better results are obtained on use of them in a lightemitting layer. A freedom of design of the recombination/light emittingregion is available by controlling the film thickness in considerationof the carrier mobility and carrier density (which is dependent onionization potential and electron affinity) of the light emitting layer,hole injecting and transporting layer, and electron injecting andtransporting layer to be combined. This enables free design of luminouscolor, control of the luminance and spectrum of light emission by theinterference of the electrodes, and control of the space distribution oflight emission.

[0230] Quinoxaline Compounds

[0231] A still further class of organic compounds useful as the hostmaterial according to the invention are quinoxaline compounds of thefollowing formula (IV).

Q_(n)-L₁₀₁  (IV)

[0232] Herein Q is a pyrazinyl radical having fused thereto asix-membered aromatic ring containing 0 to 2 nitrogen atoms and may bethe same or different, and n is 2 or 3. Two or three Q radicals may bethe same or different. The six-membered aromatic rings forming part of Qare preferably benzene, pyridine, pyrimidine and pyridazine rings. Sucha six-membered aromatic ring may be fused to the pyrazine ring at anypositions although it is preferred that carbon atoms be present andnitrogen atoms be absent at the fusion positions. It is thereforepreferred that fusion be on the side between the 2 and 3-positions or 5and 6-positions on the pyrazine ring, and on the side between the 2 and3-positions (or 5 and 6-positions) or the side between the 3 and4-positions (or 4 and 5-positions) on the pyridine ring, on the sidebetween the 4 and 5-positions (or 5 and 6-positions) on the pyrimidinering, and on the side between the 3 and 4-positions (or 5 and6-positions) or the side between the 5 and 4-positions on the pyridazinering.

[0233] L₁₀₁ is a single bond or n-valent radical, i.e., di- or trivalentradical. Preferred divalent radicals are arenediyl radicals, such asphenylene, biphenyldiyl, naphthalenediyl, anthracenediyl and pyrenediyl.Preferred trivalent radicals are arenetriyl radicals (e.g.,benzenetriyl), nitrogen atoms, and triarylaminetriyl radicals (e.g.,triphenylaminetriyl).

[0234] The radicals represented by Q and L₁₀₁ may further havesubstituents. Such substituents may be ones containing Q therein. Thetotal number of Q radicals per molecule should preferably be 2 to 10,more preferably 2 to 4. Two or more Q radicals included in one moleculemay be the same or different although they are often the same for thesake of easy synthesis.

[0235] Of the quinoxaline compounds of formula (IV), those of formula(VIII) are preferred.

[0236] In formula (VIII), Z is a group of atoms necessary to form abenzene, pyridine, pyrimidine or pyridazine ring with the two carbonatoms of the pyrazine ring.

[0237] The ring completed by Z may further have a substituent(s) or afused ring. The preferred positions of fusion of the ring completed by Zto the pyrazine ring are the same as described above in conjunction withformula (IV).

[0238] A is a monovalent substituent attached to the pyrazine ring, andk is 0, 1 or 2. Preferred examples of the substituents on the ringcompleted by Z and the substituents represented by A are the same as A₁₃etc. in formulas (VIII-a) to (VIII-m) to be described later and will bedescribed later.

[0239] The letter n is 2 or 3. When n is 2, L₁₀₁ is a single bond,phenylene, biphenyldiyl or naphthalenediyl radical. When n is 3, L₁₀₁ isa benzenetriyl radical, nitrogen atom or triphenylaminetriyl radical.These radicals will be described later in conjunction with formulas(VIII-a) to (VIII-m).

[0240] The rings completed by Z may be the same or different althoughthey are preferably the same as described in conjunction with formula(IV).

[0241] The fused pyrazine ring having the ring completed by Z may bebonded, at any position, to L₁₀₁.

[0242] Of the quinoxaline compounds of formula (VIII), those of formulas(VIII-a) to (VIII-m) are preferred.

[0243] First described are those compounds wherein L₁₀₁ in formula(VIII) is a divalent radical L₁₁₁ or single bond, as represented byformulas (VIII-a) to (VIII-f) and (VIII-m).

[0244] In formulas (VIII-a) to (VIII-f) and (VIII-m), L₁₁₁ is aphenylene, biphenyldiyl or naphthalenediyl radical. The phenyleneradical represented by L₁₁₁ may be an o-, m- or p-phenylene radical,with the p-phenylene being especially preferred. The preferredbiphenyldiyl radical represented by L₁₁₁ is 4,4′-biphenyl-1,1′-diyl. Thepreferred naphthalenediyl radical represented by L₁₁₁ is1,5-naphthalenediyl. These divalent radicals are preferablyunsubstituted although they may have substituents such as alkyl and arylgroups.

[0245] A₁₃, A₁₅ to A₁₈, A₂₃, A₂₅ to A₂₈ in formula (VIII-a), A₁₃, A₁₆ toA₁₈, A₂₃, A₂₆ to A₂₈ in formula (VIII-b), A₁₃, A₁₅, A₁₇, A₁₈, A₂₃, A₂₅,A₂₇ and A₂₈ in formula (VIII-c), A₁₃, A₁₆, A₁₈, A₂₃, A₂₆ and A₂₈ informula (VIII-d), A₁₃, A₁₇, A₁₈, A₂₃, A₂₇ and A₂₈ in formula (VIII-e),A₁₃, A₁₅, A₁₈, A₂₃, A₂₅ and A₂₈ in formula (VIII-f), A₁₂, A₁₃, A₁₅, A₁₇,A₁₈, A₂₂, A₂₃, A₂₅, A₂₇ and A₂₈ in formula (VIII-m) each independentlystand for hydrogen, halogen atoms, hydroxyl, carboxy, nitro, cyano,alkyl, aryl, alkoxy, aryloxy, amino, alkylthio, arylthio andheterocyclic radicals. In each formula, these radicals may be the sameor different.

[0246] Examples of the halogen atoms represented by A₁₃ etc. includefluorine and chlorine atoms.

[0247] The alkyl radicals represented by A₁₃ etc. are preferably thoseof 1 to 6 carbon atoms in total, which may be straight or branched. Thealkyl radicals are preferably unsubstituted ones although they may havesubstituents such as halogen atoms (e.g., F and Cl). Illustrativeexamples of the alkyl radicals include methyl, ethyl, n-propyl,isopropyl, n-butyl, isobutyl, sec-butyl, t-butyl, pentyl and hexyl.

[0248] The aryl radicals represented by A₁₃ etc. are preferably those of6 to 30 carbon atoms in total, which may be monocyclic or polycyclic(fused ring or ring collection) or have substituents. Such substituentsare halogen atoms (e.g., F and Cl), alkyl groups (e.g., methyl) andheterocyclic groups. The heterocyclic groups as the substituent arepreferably the same as the fused pyrazinyl radical bonded to L₁₁₁ informula (VIII-a), such as quinoxalinyl. Illustrative examples of thearyl radicals represented by A₁₃, etc. include phenyl, 1-naphthyl,2-naphthyl, 2-biphenylyl, 3-biphenylyl, and 4-biphenylyl radicals, whichmay have substituted thereon a fused pyradinyl group such asquinoxalinyl.

[0249] The alkoxy radicals represented by A₁₃, etc. are preferably thoseof alkyls of 1 to 6 carbon atoms in total. The alkoxy radicals arepreferably unsubstituted ones although they may have substituents.Illustrative examples of the alkoxy radicals include methoxy, ethoxy,propoxy, isopropoxy, butoxy, isobutoxy, sec-butoxy and t-butoxy.

[0250] Exemplary of the aryloxy radicals represented by A₁₃, etc. isphenoxy.

[0251] The amino radicals represented by A₁₃, etc. may have substituentssuch as alkyl and aryl groups. Exemplary amino radicals are amino,methylamino, dimethylamino, phenylamino and diphenylamino.

[0252] Examples of the alkylthio radical represented by A₁₃, etc.include methylthio and ethylthio.

[0253] Exemplary of the arylthio radical represented by A₁₃, etc. isphenylthio.

[0254] Examples of the heterocyclic radicals represented by A₁₃, etc.include furyl, thienyl, pyrrole, pyridyl, and quinolyl as well as thesame as the fused pyradinyl radical bonded to L₁₁₁ in formula (VIII-a)such as quinoxalinyl.

[0255] Two adjoining ones among A₁₅ to A₁₈ and A₂₅ to A₂₈ in formula(VIII-a), two adjoining ones among A₁₆ to A₁₈ and A₂₆ to A₂₈ in formula(VIII-b), a pair of A₁₇ and A₁₈ or a pair of A₂₇ and A₂₈ in formula(VIII-c), a pair of A₁₇ and A₁₈ or a pair of A₂₇ and A₂₈ in formula(VIII-e), and a pair of A₁₂ and A₁₃, a pair of A₁₇ and A₁₈, a pair ofA₂₂ and A₂₃ or a pair of A₂₇ and A₂₈ in formula (VIII-m) may bondtogether to form a ring. The ring formed herein is preferably a benzenering. Two or more benzene rings thus formed may be fused together, orthe benzene ring thus formed may further have a ring fused thereto.

[0256] In preferred embodiments, A₁₃ and A₂₃ in formulas (VIII-a) to(VIII-f) and A₁₂, A₁₃, A₂₂ and A₂₃ in formula (VIII-m) are arylradicals; A₁₅ to A₁₈ and A₂₅ to A₂₈ in formula (VIII-a) are hydrogen,alkyl or alkoxy radicals or two adjoining ones thereof bond together toform a benzene ring; and A₁₆ to A₁₈ and A₂₆ to A₂₈ in formula (VIII-b),A₁₅, A₁₇, A₁₈, A₂₅, A₂₇ and A₂₈ in formula (VIII-c), A₁₆, A₁₈, A₂₆ andA₂₈ in formula (VIII-d), A₁₇, A₁₈, A₂₇ and A₂₈ in formula (VIII-e), A₁₅,A₁₈, A₂₅ and A₂₈ in formula (VIII-f), and A₁₅, A₁₇, A₁₈, A₂₅, A₂₇ andA₂₈ in formula (VIII-m) are hydrogen.

[0257] Described next are those compounds wherein L₁₀₁ in formula (VIII)is a trivalent radical L₁₁₂, as represented by formulas (VIII-g) to(VIII-l).

[0258] In formulas (VIII-g) to (VIII-l), L₁₁₂ is a benzenetriyl radical,nitrogen atom or triphenylaminetriyl radical. The preferred benzenetriylradical represented by L₁₁₂ is 1,3,5-benzenetriyl. The preferredtriphenylaminetriyl radical represented by L₁₁₂ is4,4′,4″-triphenyl-1,1′,1″-triyl. These trivalent radicals are preferablyunsubstituted although they may have substituents such as alkyl and arylgroups.

[0259] A₁₃, A₁₅ to A₁₈, A₂₃, A₂₅ to A₂₈, A₃₃, A₃₅ to A₃₈ in formula(VIII-g), A₁₃, A₁₆ to A₁₈, A₂₃, A₂₆ to A₂₈, A₃₃, A₃₆ to A₃₈ in formula(VIII-h), A₁₃, A₁₅, A₁₇, A₁₈, A₂₃, A₂₅, A₂₇, A₂₈, A₃₃, A₃₅, A₃₇ and A₃₈in formula (VIII-i), A₁₃, A₁₆, A₁₈, A₂₃, A₂₆, A₂₈, A₃₃, A₃₆ and A₃₈ informula (VIII-j), A₁₃, A₁₇, A₁₈, A₂₃, A₂₇, A₂₈, A₃₃, A₃₇ and A₃₈ informula (VIII-k), A₁₃, A₁₅, A₁₈, A₂₃, A₂₅ A₂₈, A₃₃, A₃₅ and A₃₈ informula (VIII-l) each independently stand for hydrogen, halogen atoms,hydroxyl, carboxy, nitro, cyano, alkyl, aryl, alkoxy, aryloxy, amino,alkylthio, arylthio and heterocyclic radicals. In each formula, theseradicals may be the same or different. Illustrative examples of theseradicals are the same as described above in conjunction with formulas(VIII-a) to (VIII-f).

[0260] Two adjoining ones among A₁₅ to A₁₈, A₂₅ to A₂₈ and A₃₅ to A₃₈ informula (VIII-g), two adjoining ones among A₁₆ to A₁₈, A₂₆ to A₂₈ andA₃₆ to A₃₈ in formula (VIII-h), a pair of A₁₇ and A₁₈ or a pair of A₂₇and A₂₈, or a pair of A₃₇ and A₃₈ in formula (VIII-i), and a pair of A₁₇and A₁₈, a pair of A₂₇ and A₂₈ or a pair of A₃₇ and A₃₈ in formula(VIII-k) may bond together to form a ring. Illustrative examples of thering are the same as described above in conjunction with formulas(VIII-a) to (VIII-f). A₁₃, A₂₃ and A₃₃ in formulas (VIII-a) to (VIII-l)are preferably hydrogen and aryl radicals such as phenyl.

[0261] In preferred embodiments, A₁₅ to A₁₈, A₂₅ to A₂₈ and A₃₅ to A₃₈in formula (VIII-g) are hydrogen, or two adjoining ones among them bondtogether to form a ring; A₁₆ to A₁₈, A₂₆ to A₂₈, and A₃₆ to A₃₈ informula (VIII-h), A₁₅, A₁₇, A₁₈, A₂₅, A₂₇, A₂₈, A₃₅, A₃₇ and A₃₈ informula (VIII-i), A₁₆, A₁₈, A₂₆, A₂₈, A₃₆ and A₃₈ in formula (VIII-j),A₁₇, A₁₈, A₂₇, A₂₈, A₃₇ and A₃₈ in formula (VIII-k), A₁₅, A₁₈, A₂₅ A₂₈,A₃₅ and A₃₈ in formula (VIII-l) are hydrogen.

[0262] Illustrative, non-limiting, examples of the quinoxaline compoundsof formula (IV) are given below. They are shown by combinations of L₁₁₁,L₁₁₂, and A's in formulas (VIII-a) to (VIII-m). When A₁₃ and A₂₃ aredifferent, they are individually shown. The expressions of formulas(VIII-a) to (VIII-m) are typical examples and to be construed toencompass corresponding structural isomers because an actual product assynthesized is a mixture of structural isomers due to the synthesisroute. Formula (VIII) Compound No. L₁₁₁ A₁₃═A₂₃ A₁₅═A₁₅ A₁₆═A₂₆ A₁₇═A₂₇A₁₈═A₂₈ VIII-a-1

—Ph H H H H VIII-a-2

—Ph H H CH₃ H VIII-a-3

—Ph H CH₃ CH₃ H VIII-a-4

—Ph H H C₂H₅ H VIII-a-5

—Ph H H n-C₃H₇ H VIII-a-6

—Ph H H n-C₄H₉ H VIII-a-7

—Ph H H t-C₄H₉ H VIII-a-8

—Ph H H —OCH₃ H VIII-a-9

—Ph H H A₁₇ and A₁₈ form a benzene ring. A₂₇ A₂₈ form a benzene ringVIII-a-10

—Ph H A₁₆ and A₁₇ form a benzene ring. A₂₆ and A₂₇ form a benzene ring.H VIII-a-11

—Ph A₁₅ and A₁₆ form a benzene ring. A₂₅ and A₂₆ form a benzene ring A₁₇and A₁₈ form a benzene ring. A₂₇ and A₂₈ form a benzene ring. VIII-a-12

—Ph H A₁₆ and A₁₈, and A₁₇ and A₁₈ form benzene rings, respectively,which are fused to form a phenalene ring as a whole. (The same appliesto A₂₆ to A₂₈.) VIII-a-13

—Ph A₁₅ and A₁₆, A₁₆ and A₁₇, and A₁₇ and A₁₈ form benzene rings,respectively, which form a phenanthrene ring as a whole. (The sameapplies to A₂₅ to A₂₈.) VIII-a-14

—Ph H H —Ph H VIII-a-15

—Ph H —Ph —Ph H VIII-a-16

—Ph —Ph H H —Ph VIII-a-17

—Ph H H 1-naphthyl H VIII-a-18

—Ph H H 2-naphthyl H VIII-a-19

—Ph H H 4-biphenylyl H VIII-a-20

—Ph H H 3-biphenylyl H VIII-a-21

—Ph H H 2-biphenylyl H VIII-a-22

—Ph H 4-biphenylyl 4-biphenylyl H VIII-a-23

—Ph H H Cl H VIII-a-24

—Ph H H —OH H VIII-a-25

—Ph H H —NO₂ H VIII-a-26

—Ph H H —CN H VIII-a-27

—Ph H H —OPh H VIII-a-28

—Ph H H —SCH₃ H VIII-a-29

—Ph H H —SPh H VIII-a-30

—Ph H H H H VIII-a-31

—Ph H H CH₃ H VIII-a-32

—Ph H CH₃ CH₃ H VIII-a-33

—Ph CH₃ H H CH₃ VIII-a-34

—Ph H H C₂H₅ H VIII-a-35

—Ph H H n-C₃H₇ H VIII-a-36

—Ph H H n-C₄H₉ H VIII-a-37

—Ph H H t-C₄H₉ H VIII-a-38

—Ph H H —OCH₃ H VIII-a-39

—Ph H H A₁₇ and A₁₈ form a benzene ring. A₂₇ and A₂₈ form a benzenering. VIII-a-40

—Ph H A₁₆ and A₁₇ form a benzene ring. A₂₆ and A₂₇ form a benzene ring HVIII-a-41

—Ph A₁₅ and A₁₆ form a benzene ring. A₂₅ and A₂₆ form a benzen ring. A₁₇and A₁₈ form a benzene ring. A₂₇ and A₂₈ form a benzene ring. VIII-a-42

—Ph H A₁₆ and A_(18 +L, and A) ₁₇ and A₁₈ form benzene rings,respectively, which are fused to form a phenalene ring as a whole. (Thesame applies to A_(26 to A) ₂₈ .) VIII-a-43

—Ph A₁₅ and A_(16 +L, A) ₁₆ and A₁₇ , and A₁₇ and A₁₈ form benzenerings, respectively, which form a phenanthrene ring as a whole. (Thesame applies to A₂₅ to A₂₈ .) VIII-a-44

—Ph H H —Ph H VIII-a-45

—Ph H —Ph —Ph H VIII-a-46

—Ph —Ph H H —Ph VIII-a-47

—Ph H H 1-naphthyl H VIII-a-48

—Ph H H 2-naphthyl H VIII-a-49

—Ph H H 4-biphenylyl H VIII-a-50

—Ph H H 3-biphenylyl H VIII-a-51

—Ph H H 2-biphenylyl H VIII-a-52

—Ph H H Cl H VIII-a-53

—Ph H H —OH H VIII-a-54

—Ph H H —NO₂ H VIII-a-55

—Ph H H —CN H VIII-a-56

—Ph H H —OPh H VIII-a-57

—Ph H H —SCH₃ H VIII-a-58

—Ph H H —SPh H VIII-a-59

—Ph H H H H VIII-a-60

—Ph H H CH₃ H VIII-a-61

—Ph H CH₃ CH₃ H VIII-a-62

—Ph CH₃ H H CH₃ VIII-a-63

—Ph CH₃ CH₃ CH₃ H VIII-a-64

—Ph CH₃ CH₃ CH₃ CH₃ VIII-a-65

—Ph H H C₂H₅ H VIII-a-66

—Ph H H n-C₃H₇ H VIII-a-67

—Ph H H n-C₄H₉ H VIII-a-68

—Ph H H t-C₄H₉ H VIII-a-69

—Ph H H —OCH₃ H VIII-a-70

—Ph H H A₁₇ and A₁₈ form a benzene ring. A₂₇ and A₂₈ form a benzenering. VIII-a-71

—Ph H A₁₆ and A₁₇ form a benzene ring. A₂₆ and A₂₇ form a benzene ring.H VIII-a-72

—Ph A₁₅ and A₁₆ form a benzene ring. A₂₅ and A₂₆ form a benzene ring.A₁₇ and A₁₈ form a benzene ring. A₂₇ and A₂₈ form a benzene ringVIII-a-73

—Ph H A₁₆ and A_(18 +L, and A) ₁₇ and A₁₆ form benzene rings,respectively, which are fused to form a phenalene ring as a whole. (Thesame applies to A₂₆ to A₂₆ .) VIII-a-74

—Ph A₁₅ and A_(16 +L, A) ₁₆ and A₁₇ , and A₁₇ and A₁₈ form benzenerings, respectively, which form a phenanthrene ring as a whole. (Thesame applies to A₂₅ to A₂₈ .) VIII-a-75

—Ph H H —Ph H VIII-a-76

—Ph H —Ph —Ph H VIII-a-77

—Ph —Ph H H —Ph VIII-a-78

—Ph H H 1-naphthyl H VIII-a-79

—Ph H H 2-naphthyl H VIII-a-80

—Ph H H 4-biphenylyl H VIII-a-81

—Ph H H 3-biphenylyl H VIII-a-82

—Ph H H 2-biphenylyl H VIII-a-83

—Ph H H Cl H VIII-a-84

—Ph H H —OH H VIII-a-85

—Ph H H —NO₂ H VIII-a-86

—Ph H H —CN H VIII-a-87

—Ph H H —OPh H VIII-a-88

—Ph H H —SCH₃ H VIII-a-89

—Ph H H —SPh H VIII-a-90

H H H H VIII-a-91

A₂₃ = —Ph A₁₅ and A₁₆ form a benzene ring. A₂₅ and A₂₆ form a benzenring. H H VIII-a-92

A₁₅ and A₁₆ form a benzene ring. A₂₅ and A₂₆ form a benzene ring. A₁₇and A₁₈ form a benzene ring. A₂₇ and A₂₈ form a benzene ring. A₂₃ = —PhVIII-a-93

H H H H A₂₃ = —Ph VIII-a-94

A₁₅ and A₁₆ form a benzene ring. A₂₅ and A₂₆ form a benzene ring. H HA₂₃ = —Ph VIII-a-95

A₁₅ and A₁₆ form a benzene ring. A₂₅ and A₂₆ form a benzene ring. A₁₇and A₁₈ form a benzene ring. A₂₇ and A₂₈ form a benzene ring. A₂₃ = —PhVIII-a-96

—Ph H H —NPh₂ H VIII-a-97

—Ph H H —COOH H VIII-a-98

—Ph H H 2-pyridyl H VIII-a-99

—Ph H H —NPh₂ H VIII-a-100

—Ph H H —COOH H VIII-a-101

—Ph H H 2-pyridyl H VIII-a-102

—Ph H H —NPh₂ H VIII-a-103

—Ph H H —COOH H VIII-a-104

—Ph H H 2-pyridyl H Formula (VIII) Compound No. L₁₁₁ A₁₃ ═A₂₃ A₁₆═A₂₆A₁₇═A₂₇ A₁₈═A₂₈ VIII-b-1

—Ph H H H VIII-b-2

—Ph H H H VIII-b-3

—Ph H H H VIII-b-4

H H H A₂₃ = —Ph VIII-b-5

H H H A₂₃ = —Ph VIII-b-6

—Ph H H CH₃ VIII-b-7

—Ph H CH₃ H VIII-b-8

—Ph CH₃ H H VIII-b-9

—Ph H C₂H₅ H VIII-b-10

—Ph H n-C₃H₇ H VIII-b-11

—Ph H n-C₄H₉ H VIII-b-12

—Ph H t-C₄H₉ H VIII-b-13

—Ph H —OCH₃ H VIII-b-14

—Ph A₁₆ and A₁₇ form a benzene ring. A₂₆ and A₂₇ form a benzene ring. HVIII-b-15

—Ph H A₁₇ and A₁₈ form a benzene ring. Ahd 27 and A₂₈ form a benzenering. VIII-b-16

—Ph H Ph H VIII-b-17

—Ph Ph Ph H VIII-b-18

—Ph H 1-naphthyl H VIII-b-19

—Ph 1-naphthyl 1-naphthyl H VIII-b-20

—Ph H 2-naphthyl H VIII-b-21

—Ph 2-naphthyl 2-naphthyl H VIII-b-22

—Ph H 4-biphenylyl H VIII-b-23

—Ph 4-biphenylyl 4-biphenylyl H VIII-b-24

—Ph H 3-biphenylyl H VIII-b-25

—Ph 3-biphenylyl 3-biphenylyl H VIII-b-26

—Ph H 2-biphenylyl H VIII-b-27

—Ph 2-biphenylyl 2-biphenylyl H VIII-b-28

—Ph H Cl H VIII-b-29

—Ph H —OH H VIII-b-30

—Ph H —NO₂ H VIII-b-31

—Ph H —CN H VIII-b-32

—Ph H —OPh H VIII-b-33

—Ph H —SCH₃ H VIII-b-34

—Ph H —SPh H VIII-b-35

—Ph H —NPh₂ H VIII-b-36

—Ph H —COOH H VIII-b-37

—Ph H 2-pyridyl H VIII-b-38

—Ph H H CH₃ VIII-b-39

—Ph H CH₃ H VIII-b-40

—Ph CH₃ H H VIII-b-41

—Ph H C₂H₅ H VIII-b-42

—Ph H n-C₃H₇ H VIII-b-43

—Ph H n-C₄H₉ H VIII-b-44

—Ph H t-C₄H₉ H VIII-b-45

—Ph H —OCH₃ H VIII-b-46

—Ph A₁₆ and A₁₇ form a benzene ring. A₂₆ and A₂₇ form a benzene ring. HVIII-b-47

—Ph H A₁₇ and A₁₈ form a benzene ring. A₂₇ and A₂₈ form a benzene ring.VIII-b-48

—Ph H Ph H VIII-b-49

—Ph Ph Ph H VIII-b-50

—Ph H 1-naphthyl H VIII-b-51

—Ph 1-naphthyl 1-naphthyl H VIII-b-52

—Ph H 2-naphthyl H VIII-b-53

—Ph 2-naphthyl 2-naphthyl H VIII-b-54

—Ph H 4-biphenylyl H VIII-b-55

—Ph 4-biphenylyl 4-biphenylyl H VIII-b-56

—Ph H 3-biphenylyl H VIII-b-57

—Ph 3-biphenylyl 3-biphenylyl H VIII-b-58

—Ph H 2-biphenylyl H VIII-b-59

—Ph 2-biphenylyl 2-biphenylyl H VIII-b-60

—Ph H Cl H VIII-b-61

—Ph H —OH H VIII-b-62

—Ph H —NO₂ H VIII-b-63

—Ph H —CN H VIII-b-64

—Ph H —OPh H VIII-b-65

—Ph H —SCH₃ H VIII-b-66

—Ph H —SPh H VIII-b-67

—Ph H —NPh₂ H VIII-b-68

—Ph H —COOH H VIII-b-69

—Ph H 2-pyridyl H VIII-b-70

—Ph H H CH₃ VIII-b-71

—Ph H CH₃ H VIII-b-72

—Ph CH₃ H H VIII-b-73

—Ph H C₂H₅ H VIII-b-74

—Ph H n-C₃H₇ H VIII-b-75

—Ph H n-C₄H₉ H VIII-b-76

—Ph H H t-C₄H₉ VIII-b-77

—Ph H t-C₄H₉ H VIII-b-78

—Ph H —OCH₃ H VIII-b-79

—Ph A₁₆ and A₁₇ form a benzene ring. A₂₆ and A₂₇ form a benzene ring. HVIII-b-80

—Ph H A₁₇ and A₁₈ form a benzene ring. A₂₇ and A₂₈ form a benzene ring.VIII-b-81

—Ph H —Ph H VIII-b-82

—Ph Ph Ph H VIII-b-83

—Ph H 1-naphthyl H VIII-b-84

—Ph 1-naphthyl 1-naphthyl H VIII-b-85

—Ph H 2-naphthyl H VIII-b-86

—Ph 2-naphthyl 2-naphthyl H VIII-b-87

—Ph H 4-biphenylyl H VIII-b-88

—Ph 4-biphenylyl 4-biphenylyl H VIII-b-89

—Ph H 3-biphenylyl H VIII-b-90

—Ph 3-biphenylyl 3-biphenylyl H VIII-b-91

—Ph H 2-biphenylyl H VIII-b-92

—Ph 2-biphenylyl 2-biphenylyl H VIII-b-93

—Ph H Cl H VIII-b-94

—Ph H —OH H VIII-b-95

—Ph H —NO₂ H VIII-b-96

—Ph H —CN H VIII-b-97

—Ph H —OPh H VIII-b-98

—Ph H —SCH₃ H VIII-b-99

—Ph H —SPh H VIII-b-100

—Ph H —NPh₂ H VIII-b-101

—Ph H —COOH H VIII-b-102

—Ph H 2-pyridyl H Formula (VIII) Compound No. L₁₁₁ A₁₃═A₂₃ A₁₅═A₂₅A₁₇═A₂₇ A₁₈═A₂₈ VIII-c-1

—Ph H H H VIII-c-2

—Ph H H H VIII-c-3

—Ph H H H VIII-c-4

H H H A₂₃ = —Ph VIII-c-5

H H H A₂₃ = —Ph VIII-c-6

—Ph H H CH₃ VIII-c-7

—Ph H CH₃ H VIII-c-8

—Ph CH₃ H H VIII-c-9

—Ph H C₂H₅ H VIII-c-10

—Ph H n-C₃H₇ H VIII-c-11

—Ph H n-C₄H₉ H VIII-c-12

—Ph H t-C₄H₉ H VIII-c-13

—Ph H —OCH₃ H VIII-c-14

—Ph H A₁₇ and A₁₈ form a benzene ring. A₂₇ and A₂₈ form a beozene ring.VIII-c-15

—Ph H H —Ph VIII-c-16

—Ph H —Ph H VIII-c-17

—Ph —Ph H H VIII-c-18

—Ph H 1-naphthyl H VIII-c-19

—Ph H 2-naphthyl H VIII-c-20

—Ph H 4-biphenylyl H VIII-c-21

—Ph H 3-biphenylyl H VIII-c-22

—Ph H 2-biphenylyl H VIII-c-23

—Ph H Cl H VIII-c-24

—Ph H —OH H VIII-c-25

—Ph H —NO₂ H VIII-c-26

—Ph H —CN H VIII-c-27

—Ph H —OPh H VIII-c-28

—Ph H —SCH₃ H VIII-c-29

—Ph H —SPh H VIII-c-30

—Ph H —NPh₂ H VIII-c-31

—Ph H —COOH H VIII-c-32

—Ph H 2-pyridyl H VIII-c-33

—Ph H H CH₃ VIII-c-34

—Ph H CH₃ H VIII-c-35

—Ph CH₃ H H VIII-c-36

—Ph H C₂H₅ H VIII-c-37

—Ph H n-C₃H₇ H VIII-c-38

—Ph H n-C₄H₉ H VIII-c-39

—Ph H t-C₄H₉ H VIII-c-40

—Ph —OCH₃ H H VIII-c-41

—Ph H A₁₇ and A₁₈ form a benzene ring. A₂₇ and A₂₈ form a benzene ring.VIII-c-42

—Ph H H —Ph VIII-c-43

—Ph H —Ph H VIII-c-44

—Ph —Ph H H VIII-c-45

—Ph H 1-naphthyl H VIII-c-46

—Ph H 2-naphthyl H VIII-c-47

—Ph H 4-biphenylyl H VIII-c-48

—Ph H 3-biphenylyl H VIII-c-49

—Ph H 2-biphenylyl H VIII-c-50

—Ph H Cl H VIII-c-51

—Ph H —OH H VIII-c-52

—Ph H —NO₂ H VIII-c-53

—Ph H —CN H VIII-c-54

—Ph H —OPh H VIII-c-55

—Ph H —SCH₃ H VIII-c-56

—Ph H —SPh H VIII-c-57

—Ph H —NPh₂ H VIII-c-58

—Ph H —COOH H VIII-c-59

—Ph H 2-pyridyl H VIII-c-60

—Ph H H CH₃ VIII-c-61

—Ph H CH₃ H VIII-c-62

—Ph CH₃ H H VIII-c-63

—Ph H C₂H₅ H VIII-c-64

—Ph H n-C₃H₇ H VIII-c-65

—Ph H n-C₄H₉ H VIII-c-66

—Ph H t-C₄H₉ H VIII-c-67

—Ph H —OCH₃ H VIII-c-68

—Ph H A₁₇ and A₁₈ form a benzene ring. A₂₇ and A₂₈ form a benzene ring.VIII-c-69

—Ph H H —Ph VIII-c-70

—Ph H —Ph H VIII-c-71

—Ph —Ph H H VIII-c-72

—Ph H 1-naphthyl H VIII-c-73

—Ph H 2-naphthyl H VIII-c-74

—Ph H 4-biphenylyl H VIII-c-75

—Ph H 2-biphenylyl H VIII-c-76

—Ph H Cl H VIII-c-77

—Ph H —OH H VIII-c-78

—Ph H —NO₂ H VIII-c-79

—Ph H —CN H VIII-c-80

—Ph H —OPh H VIII-c-81

—Ph H —SCH₃ H VIII-c-82

—Ph H —SPh H VIII-c-83

—Ph H —NPh₂ H VIII-c-84

—Ph H —COOH H VIII-c-85

—Ph H 2-pyridyl H Formula (VIII) Compound No. L₁₁₁ A₁₃ ═A₂₃ A₁₆═A₂₆A₁₈═A₂₈ VIII-d-1

—Ph H H VIII-d-2

—Ph H H VIII-d-3

—Ph H H VIII-d-4

H H A₂₃ = —Ph VIII-d-5

H H A₂₃ = —Ph VIII-d-6

—Ph H CH₃ VIII-d-7

—Ph CH₃ H VIII-d-8

—Ph CH₃ CH₃ VIII-d-9

—Ph C₂H₅ H VIII-d-10

—Ph n-C₃H₇ H VIII-d-11

—Ph n-C₄H₉ H VIII-d-12

—Ph t-C₄H₉ H VIII-d-13

—Ph —OCH₃ H VIII-d-14

—Ph H —Ph VIII-d-15

—Ph —Ph H VIII-d-16

—Ph 1-naphthyl H VIII-d-17

—Ph 2-naphthyl H VIII-d-18

—Ph 4-biphenylyl H VIII-d-19

—Ph 3-biphenylyl H VIII-d-20

—Ph 2-biphenylyl H VIII-d-21

—Ph Cl H VIII-d-22

—Ph —OH H VIII-d-23

—Ph —NO₂ H VIII-d-24

—Ph —CN H VIII-d-25

—Ph —OPh H VIII-d-26

—Ph —SCH₃ H VIII-d-27

—Ph —SPh H VIII-d-28

—Ph —NH₂ H VIII-d-29

—Ph —NH—Ph H VIII-d-30

—Ph —NPh₂ H VIII-d-31

—Ph —COOH H VIII-d-32

—Ph 2-pyridyl H VIII-d-33

—Ph H CH₃ VIII-d-34

—Ph CH₃ H VIII-d-35

—Ph CH₃ CH₃ VIII-d-36

—Ph C₂H₅ H VIII-d-37

—Ph n-C₃H₇ H VIII-d-38

—Ph n-C₄H₉ H VIII-d-39

—Ph t-C₄H₉ H VIII-d-40

—Ph —OCH₃ H VIII-d-41

—Ph H —Ph VIII-d-42

—Ph —Ph H VIII-d-43

—Ph 1-naphthyl H VIII-d-44

—Ph 4-biphenylyl H VIII-d-45

—Ph 3-biphenylyl H VIII-d-46

—Ph 2-biphenylyl H VIII-d-47

—Ph Cl H VIII-d-48

—Ph —OH H VIII-d-49

—Ph NO₂ H VIII-d-50

—Ph —CN H VIII-d-51

—Ph —OPh H VIII-d-52

—Ph —SCH₃ H VIII-d-53

—Ph —SPh H VIII-d-54

—Ph —NPh₂ H VIII-d-55

—Ph —COOH H VIII-d-56

—Ph 2-pyridyl H VIII-d-57

—Ph H CH₃ VIII-d-58

—Ph CH₃ H VIII-d-59

—Ph CH₃ CH₃ VIII-d-60

—Ph H C₂H₅ VIII-d-61

—Ph C₂H₅ H VIII-d-62

—Ph n-C₃H₇ H VIII-d-63

—Ph n-C₄H₉ H VIII-d-64

—Ph t-C₄H₉ H VIII-d-65

—Ph H —OCH₃ VIII-d-66

—Ph —OCH₃ H VIII-d-67

—Ph —OCH₃ —OCH₃ VIII-d-68

—Ph H —Ph VIII-d-69

—Ph —Ph H VIII-d-70

—Ph H 1-naphthyl VIII-d-71

—Ph 1-naphthyl H VIII-d-72

—Ph 2-naphthyl H VIII-d-73

—Ph H 4-biphenylyl VIII-d-74

—Ph 4-biphenylyl H VIII-d-75

—Ph 3-biphenylyl H VIII-d-76

—Ph 2-biphenylyl H VIII-d-77

—Ph Cl H VIII-d-78

—Ph —OH H VIII-d-79

—Ph —NO₂ H VIII-d-80

—Ph —CN H VIII-d-81

—Ph —OPh H VIII-d-82

—Ph —SCH₃ H VIII-d-83

—Ph —SPh H VIII-d-84

—Ph —NPh₂ H VIII-d-85

—Ph —COOH H VIII-d-86

—Ph 2-pyridyl H Formula (VIII) Compound No. L₁₁₁ A₁₃═A₂₃ A₁₇═A₂₇ A₁₈═A₂₈VIII-e-1

—Ph H H VIII-e-2

—Ph H H VIII-e-3

—Ph H H VIII-e-4

—Ph H CH₃ VIII-e-5

—Ph CH₃ H VIII-e-6

—Ph CH₃ CH₃ VIII-e-7

—Ph C₂H₅ H VIII-e-8

—Ph n-C₃H₇ H VIII-e-9

—Ph n-C₃H₇ n-C₃H₇ VIII-e-10

—Ph n-C₄H₉ H VIII-e-11

—Ph t-C₄H₉ H VIII-e-12

—Ph —OCH₃ H VIII-e-13

—Ph A₁₇ and A₁₈ form a benzene ring. A₂₇ and A₂₈ form a benzene ring.VIII-e-14

—Ph H —Ph VIII-e-15

—Ph —Ph H VIII-e-16

—Ph —Ph —Ph VIII-e-17

—Ph 1-naphthyl H VIII-e-18

—Ph 2-naphthyl H VIII-e-19

—Ph 4-biphenylyl H VIII-e-20

—Ph 3-biphenylyl H VIII-e-21

—Ph 2-biphenylyl H VIII-e-22

—Ph Cl H VIII-e-23

—Ph —OH H VIII-e-24

—Ph —NO₂ H VIII-e-25

—Ph —CN H VIII-e-26

—Ph —OPh H VIII-e-27

—Ph —SCH₃ H VIII-e-28

—Ph —SPh H VIII-e-29

—Ph —NPh₂ H VIII-e-30

—Ph —COOH H VIII-e-31

—Ph 2-pyridyl H VIII-e-32

—Ph H CH₃ VIII-e-33

—Ph CH₃ H VIII-e-34

—Ph CH₃ CH₃ VIII-e-35

—Ph C₂H₅ H VIII-e-36

—Ph n-C₃H₇ H VIII-e-37

—Ph n-C₃H₇ n-C₃H₇ VIII-e-38

—Ph n-C₄H₉ H VIII-e-39

—Ph t-C₄H₉ H VIII-e-40

—Ph H —OCH₃ VIII-e-41

—Ph —OCH₃ H VIII-e-42

—Ph A₁₇ and A₁₈ form a benzene ring. A₂₇ and A₂₈ form a benzene ring.VIII-e-43

—Ph H —Ph VIII-e-44

—Ph —Ph H VIII-e-45

—Ph —Ph —Ph VIII-e-46

—Ph 1-naphthyl H VIII-e-47

—Ph 2-naphthyl H VIII-e-48

—Ph H 4-biphenylyl VIII-e-49

—Ph 4-biphenylyl 4-biphenylyl VIII-e-50

—Ph 3-biphenylyl H VIII-e-51

—Ph 2-biphenylyl H VIII-e-52

—Ph Cl H VIII-e-53

—Ph —OH H VIII-e-54

—Ph —NO₂ H VIII-e-55

—Ph —CN H VIII-e-56

—Ph —OPh H VIII-e-57

—Ph —SCH₃ H VIII-e-58

—Ph —SPh H VIII-e-59

—Ph —NPh₂ H VIII-e-60

—Ph —COOH H VIII-e-61

—Ph 2-pyridyl H VIII-e-62

—Ph H CH₃ VIII-e-63

—Ph CH₃ H VIII-e-64

—Ph CH₃ CH₃ VIII-e-65

—Ph C₂H₅ H VIII-e-66

—Ph n-C₃H₇ H VIII-e-67

—Ph n-C₃H₇ n-C₃H₇ VIII-e-68

—Ph n-C₄H₉ H VIII-e-69

—Ph t-C₄H₉ H VIII-e-70

—Ph t-C₄H₉ t-C₄H₉ VIII-e-71

—Ph —OCH₃ H VIII-e-72

—Ph A₁₇ and A₁₈ form a benzene ring. A₂₇ and A₂₈ form a benzene ring.VIII-e-73

—Ph H —Ph VIII-e-74

—Ph —Ph H VIII-e-75

—Ph —Ph —Ph VIII-e-76

—Ph 1-naphthyl H VIII-e-77

—Ph 2-naphthyl H VIII-e-78

—Ph 3-biphenylyl H VIII-e-79

—Ph 2-biphenylyl H VIII-e-80

—Ph Cl H VIII-e-81

—Ph —OH H VIII-e-82

—Ph —NO₂ H VIII-e-83

—Ph —CN H VIII-e-84

—Ph —OPh H VIII-e-85

—Ph —SCH₃ H VIII-e-86

—Ph —SPh H VIII-e-87

—Ph —NPh₂ H VIII-e-88

—Ph —COOH H VIII-e-89

—Ph 2-pyridyl H Formula (VIII) Compound No. L₁₁₁ A₁₃═A₂₃ A₁₅═A₂₅ A₁₈═A₂₈VIII-f-1

—Ph H H VIII-f-2

—Ph H H VIII-f-3

—Ph H H VIII-f-4

—Ph H CH₃ VIII-f-5

—Ph CH₃ H VIII-f-6

—Ph CH₃ CH₃ VIII-f-7

—Ph C₂H₅ H VIII-f-8

—Ph n-C₃H₇ H VIII-f-9

—Ph n-C₄H₉ H VIII-f-10

—Ph t-C₄H₉ H VIII-f-11

—Ph —OCH₃ H VIII-f-12

—Ph H —Ph VIII-f-13

—Ph —Ph H VIII-f-14

—Ph —Ph —Ph VIII-f-15

—Ph H 1-naphthyl VIII-f-16

—Ph 1-naphthyl H VIII-f-17

—Ph 2-naphthyl H VIII-f-18

—Ph 4-biphenylyl H VIII-f-19

—Ph 3-biphenylyl H VIII-f-20

—Ph 2-biphenylyl H VIII-f-21

—Ph Cl H VIII-f-22

—Ph —OH H VIII-f-23

—Ph —NO₂ H VIII-f-24

—Ph —CN H VIII-f-25

—Ph —OPh H VIII-f-26

—Ph —SCH₃ H VIII-f-27

—Ph —SPh H VIII-f-28

—Ph —NPh₂ H VIII-f-29

—Ph —COOH H VIII-f-30

—Ph 2-pyridyl H VIII-f-31

—Ph H CH₃ VIII-f-32

—Ph CH₃ H VIII-f-33

—Ph CH₃ CH₃ VIII-f-34

—Ph C₂H₅ H VIII-f-35

—Ph n-C₃H₇ H VIII-f-36

—Ph n-C₄H₉ H VIII-f-37

—Ph t-C₄H₉ H VIII-f-38

—Ph —OCH₃ H VIII-f-39

—Ph H —Ph VIII-f-40

—Ph —Ph H VIII-f-41

—Ph —Ph —Ph VIII-f-42

—Ph 1-naphthyl H VIII-f-43

—Ph 2-naphthyl H VIII-f-44

—Ph 4-biphenylyl H VIII-f-45

—Ph 3-biphenylyl H VIII-f-46

—Ph 2-biphenylyl H VIII-f-47

—Ph Cl H VIII-f-48

—Ph OH H VIII-f-49

—Ph —NO₂ H VIII-f-50

—Ph —CN H VIII-f-51

—Ph —OPh H VIII-f-52

—Ph —SCH₃ H VIII-f-53

—Ph —SPh H VIII-f-54

—Ph —NPh₂ H VIII-f-55

—Ph —COOH H VIII-f-56

—Ph 2-pyridyl H VIII-f-57

—Ph H CH₃ VIII-f-58

—Ph CH₃ H VIII-f-59

—Ph CH₃ CH₃ VIII-f-60

—Ph C₂H₅ H VIII-f-61

—Ph n-C₃H₇ H VIII-f-62

—Ph n-C₄H₉ H VIII-f-63

—Ph t-C₄H₉ H VIII-f-64

—Ph —OCH₃ H VIII-f-65

—Ph H —Ph VIII-f-66

—Ph —Ph H VIII-f-67

—Ph —Ph —Ph VIII-f-68

—Ph 1-naphthyl H VIII-f-69

—Ph 2-naphthyl H VIII-f-70

—Ph 4-biphenylyl H VIII-f-71

—Ph 3-biphenylyl H VIII-f-72

—Ph 2-biphenylyl H VIII-f-73

—Ph Cl H VIII-f-74

—Ph —OH H VIII-f-75

—Ph —NO₂ H VIII-f-76

—Ph —CN H VIII-f-77

—Ph —OPh H VIII-f-78

—Ph —SCH₃ H VIII-f-79

—Ph —SPh H VIII-f-80

—Ph —NPh₂ H VIII-f-81

—Ph —COOH H VIII-f-82

—Ph 2-pyridyl H Formula (VIII) A₁₃═A₂₃ A₁₅═A₂₅ A₁₆═A₂₆ A₁₇═A₂₇ A₁₈═A₂₈Compound No. L₁₁₂ ═A₃₃ ═A₃₅ ═A₃₆ ═A₃₇ A₃₈ VIII-g-1

H H H H H VIII-g-2

H A₁₅ and A₁₈ form a benzene ring. A₂₅ and A₂₆ form a benzene ring. A₃₅and A₃₆ form a benzene ring. A₁₇ and A₁₈ form a benzene ring. A₂₇ andA₂₈ form a benzene ring. A₃₇ and A₃₈ form a benzene ring. VIII-g-3

H A₁₅ and A₁₆ form a benzene ring. A₂₅ and A₂₆ form a benzene ring. A₃₅and A₃₆ form a benzene ring. H H VIII-g-4

—Ph H H H H VIII-g-5

—Ph A₁₅ and A₁₆ form a benzene ring. A₂₅ and A₂₆ form a benzene ring.A₃₅ and A₃₆ form a benzene ring. A₁₇ and A₁₈ form a benzene ring. A₂₇and A₂₈ form a benzene ring. A₃₇ and A₃₈ form a benzene ring. VIII-g-6

—Ph A₁₅ and A₁₆ form a benzene ring. A₂₅ and A₂₆ form a benzene ring.A₃₅ and A₃₆ form a benzene ring. H H VIII-g-7

H H H H H VIII-g-8

H A₁₅ and A₁₆ form a benzene ring. A₂₅ and A₂₆ form a benzene ring. A₃₅and A₃₆ form a benzene ring. A₁₇ and A₁₈ form a benzene ring. A₂₇ andA₂₈ form a benzene ring. A₃₇ and A₃₈ form a benzene ring. VIII-g-9

H A₁₅ and A₁₆ form a benzene ring. A₂₅ and A₂₆ form a benzene ring. A₃₅and A₃₆ form a benzene ring. H H VIII-g-10

—Ph H H H H VIII-g-11

—Ph A₁₅ and A₁₆ form a benzene ring. A₂₅ and A₂₆ form a benzene ring.A₃₅ and A₃₆ form a benzene ring. A₁₇ and A₁₈ form a benzene ring. A₂₇and A₂₈ form a benzene ring. A₃₇ and A₃₈ form a benzene ring. VIII-g-12

—Ph A₁₅ and A₁₅ form a benzene ring. A₂₅ and A₂₆ form a benzene ring.A₃₅ and A₃₆ form a benzene ring. H H VIII-g-13

H H H H H VIII-g-14

H A₁₅ and A₁₆ form a benzene ring. A₂₅ and A₂₆ form a benzene ring. A₃₅and A₃₆ form a benzene ring. H H VIII-g-15

H A₁₅ and A₁₆ form a benzene ring. A₂₅ and A₂₆ form a benzene ring. A₃₅and A₃₆ form a benzene ring. A₁₇ and A₁₈ form a benzene ring. A₂₇ andA₂₈ form a benzene ring. A₃₇ and A₃₈ form a benzene ring. VIII-g-16

—Ph H H H H VIII-g-17

—Ph A₁₅ and A₁₆ form a benzene ring. A₂₅ and A₂₆ form a benzene ring.A₃₅ and A₃₆ form a benzene ring. A₁₇ and A₁₈ form a benzene ring. A₂₇and A₂₈ form a benzene ring. A₃₇ and A₃₈ form a benzene ring. VIII-g-18

—Ph A₁₅ and A₁₆ form a benzene ring. A₂₅ and A₂₆ form a benzene ring.A₃₅ and A₃₆ form a benzene ring. H H VIII-g-19

—Ph H H —Ph H VIII-g-20

—Ph —Ph H H H VIII-g-21

—Ph H —Ph H H VIII-g-22

—Ph H H H —Ph VIII-g-23

—Ph H H Cl H VIII-g-24

—Ph H H —OH H VIII-g-25

—Ph H H —NO₂ H VIII-g-26

—Ph H H —CN H VIII-g-27

—Ph H H —OPh H VIII-g-28

—Ph H H —SCH₃ H VIII-g-29

—Ph H H —SPh H VIII-g-30

—Ph H H —NPh H VIII-g-31

—Ph H H CH₃ H VIII-g-32

—Ph H H —OCH₃ H VIII-g-33

—Ph H H —COOH H VIII-g-34

—Ph H H 2-pyridyl H VIII-g-35

—Ph H H —Ph H VIII-g-36

—Ph —Ph H H H VIII-g-37

—Ph H —Ph H H VIII-g-38

—Ph H H H —Ph VIII-g-39

—Ph H H Cl H VIII-g-40

—Ph H H —OH H VIII-g-41

—Ph H H —NO₂ H VIII-g-42

—Ph H H —CN H VIII-g-43

—Ph H H —OPh H VIII-g-44

—Ph H H SCH₃ H VIII-g-45

—Ph H H —SPh H VIII-g-46

—Ph H H —NPh H VIII-g-47

—Ph H H CH₃ H VIII-g-48

—Ph H H —OCH₃ H VIII-g-49

—Ph H H —COOH H VIII-g-50

—Ph H H 2-pyridyl H VIII-g-51

—Ph H H —Ph H VIII-g-52

—Ph —Ph H H H VIII-g-53

—Ph H —Ph H H VIII-g-54

—Ph H H H —Ph VIII-g-55

—Ph H H Cl H VIII-g-56

—Ph H H —OH H VIII-g-57

—Ph H H —NO₂ H VIII-g-58

—Ph H H —CN H VIII-g-59

—Ph H H —OPh H VIII-g-60

—Ph H H —SCH₃ H VIII-g-61

—Ph H H —SPh H VIII-g-62

—Ph H H —NPh H VIII-g-63

—Ph H H CH₃ H VIII-g-64

—Ph H H —OCH₃ H VIII-g-65

—Ph H H —COOH H VIII-g-66

—Ph H H 2-pyridyl H Formula (VIII) A₁₃═A₂₃ A₁₆═A₂₆ A₁₇═A₂₇ A₁₈═A₂₈Compound No. L₁₁₂ ═A₃₃ ═A₃₆ ═A₃₇ ═A₃₈ VIII-h-1

H H H H VIII-h-2

—Ph H H H VIII-h-3

H H H H VIII-h-4

—Ph H H H VIII-h-5

H H H H VIII-h-6

—Ph H H H VIII-h-7

H A₁₆ and A₁₇ form a benzene ring. A₂₆ and A₂₇ form a benzene ring. A₃₆and A₃₇ form a benzene ring. H VIII-h-8

—Ph A₁₆ and A₁₇ form a benzene ring. A₂₆ and A₂₇ form a benzene ring.A₃₆ and A₃₇ form a benzene ring. H VIII-h-9

H H A₁₇ and A₁₈ form a benzene ring. A₂₇ and A₂₈ form a benzene ring.A₃₇ and A₃₈ form a benzene ring. VIII-h-10

—Ph H A₁₇ and A₁₈ form a benzene ring. A₃₇ and A₂₈ form a benzene ring.A₃₇ and A₃₈ form a benzene ring. VIII-h-11

—Ph —Ph H H VIII-h-12

—Ph H —Ph H VIII-h-13

—Ph H H —Ph VIII-h-14

—Ph H Cl H VIII-h-15

—Ph H —OH H VIII-h-16

—Ph H —NO₂ H VIII-h-17

—Ph H —CN H VIII-h-18

—Ph H —OPh H VIII-h-19

—Ph H —SCH₃ H VIII-h-20

—Ph H —SPh H VIII-h-21

—Ph H —NPh₂ H VIII-h-22

—Ph H CH₃ H VIII-h-23

—Ph H —OCH₃ H VIII-h-24

—Ph H —COOH H VIII-h-25

—Ph H 2-pyridyl H VIII-h-26

H A₁₆ and A₁₇ form a benzene ring. A₂₆ and A₂₇ form a benzene ring. A₃₆and A₃₇ form a benzene ring. H VIII-h-27

—Ph A₁₆ and A₁₇ form a benzene ring. A₂₆ and A₂₇ form a benzene ring.A₃₆ and A₃₇ form a benzene ring. H VIII-h-28

H H A₁₇ and A₁₆ form a benzene ring. A₂₇ and A₂₈ form a benzene ring.A₃₇ and A₃₈ form a benzene ring. VIII-h-29

—Ph H A₁₇ and A₁₆ form a benzene ring. A₂₇ and A₂₈ form a benzene ring.A₃₇ and A₃₆ form a benzene ring. VIII-h-30

—Ph —Ph H H VIII-h-31

—Ph H —Ph H VIII-h-32

—Ph H H —Ph VIII-h-33

—Ph H Cl H VIII-h-34

—Ph H —OH H VIII-h-35

—Ph H —NO₂ H VIII-h-36

—Ph H —CN H VIII-h-37

—Ph H —OPh H VIII-h-38

—Ph H —SCH₃ H VIII-h-39

—Ph H —SPh H VIII-h-40

—Ph H —NPh₂ H VIII-h-41

—Ph H CH₃ H VIII-h-42

—Ph H —OCH₃ H VIII-h-43

—Ph H —COOH H VIII-h-44

—Ph H 2-pyridyl H VIII-h-45

H A₁₆ and A₁₇ form a benzene ring. A₂₆ and A₂₇ form a benzene ring. A₃₆and A₃₇ form a benzene ring. H VIII-h-46

—Ph A₁₆ and A₁₇ form a benzene ring. A₂₆ and A₂₇ form a benzene ring.A₃₆ and A₃₇ form a benzene ring. H VIII-h-47

H H A₁₇ and A₁₈ form a benzene ring. A₂₇ and A₂₈ form a benzene ring.A₃₇ and A₃₈ form a benzene ring. VIII-h-48

—Ph H A₁₇ and A₁₈ form a henzene ring. A₂₇ and A₂₈ form a benzene ring.A₃₇ and A₃₈ form a benzene ring. VIII-h-49

—Ph —Ph H H VIII-h-50

—Ph H —Ph H VIII-h-51

—Ph H H —Ph VIII-h-52

—Ph H Cl H VIII-h-53

—Ph H —OH H VIII-h-54

—Ph H —NO₂ H VIII-h-55

—Ph H —CN H VIII-h-56

—Ph H —OPh H VIII-h-57

—Ph H —SCH₃ H VIII-h-58

—Ph H —SPh H VIII-h-59

—Ph H —NPh₂ H VIII-h-60

—Ph H CH₃ H VIII-h-61

—Ph H —OCH₃ H VIII-h-62

—Ph H —COOH H VIII-h-63

—Ph H 2-pyridyl H VIII-i-1

H H H H VIII-i-2

—Ph H H H VIII-i-3

H H H H VIII-i-4

H H H H VIII-i-5

—Ph H H H VIII-i-6

H H A₁₇ and A₁₈ form a benzene ring. A₂₇ and A₂₈ form a benzene ring.A₃₇ and A₃₈ form a benzene ring. VIII-i-7

—Ph H A₁₇ and A₁₈ form a benzene ring. A₂₇ and A₂₈ form a benzene ring.A₃₇ and A₃₈ form a benzene ring. VIII-i-8

H H A₁₇ and A₁₈ form a benzene ring. A₂₇ and A₂₈ form a benzene ring.A₃₇ and A₃₈ form a benzene ring. VIII-i-9

H H A₁₇ and A₁₈ form a benzene ring. A₂₇ and A₂₈ form a benzene ring.A₃₇ and A₃₈ form a benzene ring. VIII-i-10

—Ph H A₁₇ and A₁₈ form a benzene ring. A₂₇ and A₂₈ form a benzene ring.A₃₇ and A₃₈ form a benzene ring. VIII-i-11

—Ph —Ph H H VIII-i-12

—Ph H —Ph H VIII-i-13

—Ph H H —Ph VIII-i-14

—Ph H Cl H VIII-i-15

—Ph H —OH H VIII-i-16

—Ph H —NO₂ H VIII-i-17

—Ph H —CN H VIII-i-18

—Ph H —OPh H VIII-i-19

—Ph H —SCH₃ H VIII-i-20

—Ph H —SPh H VIII-i-21

—Ph H —N—Ph₂ H VIII-i-22

—Ph H CH₃ H VIII-i-23

—Ph H —OCH₃ H VIII-i-24

—Ph H —COOH H VIII-i-25

—Ph H 2-pyridyl H VIII-i-26

—Ph —Ph H H VIII-i-27

—Ph H —Ph H VIII-i-28

—Ph H H —Ph VIII-i-29

—Ph H Cl H VIII-i-30

—Ph H —OH H VIII-i-31

—Ph H —NO₂ H VIII-i-32

—Ph H —CN H VIII-i-33

—Ph H —OPh H VIII-i-34

—Ph H —SCH₃ H VIII-i-35

—Ph H —SPh H VIII-i-36

—Ph H —N—Ph₂ H VIII-i-37

—Ph H CH₃ H VIII-i-38

—Ph H —OCH₃ H VIII-i-39

—Ph H —COOH H VIII-i-40

—Ph H 2-pyridyl H VIII-i-41

—Ph —Ph H H VIII-i-42

—Ph H —Ph H VIII-i-43

—Ph H H —Ph VIII-i-44

—Ph H Cl H VIII-i-45

—Ph H —OH H VIII-i-46

—Ph H —NO₂ H VIII-i-47

—Ph H —CN H VIII-i-48

—Ph H —OPh H VIII-i-49

—Ph H —SCH₃ H VIII-i-50

—Ph H —SPh H VIII-i-51

—Ph H —N—Ph₂ H VIII-i-52

—Ph H CH₃ H VIII-i-53

—Ph H —OCH₃ H VIII-i-54

—Ph H —COOH H VIII-i-55

—Ph H 2-pyridyl H Formula (VIII) Compound No. L₁₁₂ A₁₃ ═A₂₃═A₃₃ A₁₆═A₂₆═A₃₆ A₁₈ ═A₂₈═A₃₈ VIII-j-1

H H H VIII-j-2

—Ph H H VIII-j-3

H H H VIII-j-4

H H H VIII-j-5

—Ph H H VIII-j-6

—Ph —Ph H VIII-j-7

—Ph H —Ph VIII-j-8

—Ph Cl H VIII-j-9

—Ph —OH H VIII-j-10

—Ph —NO₂ H VIII-j-11

—Ph —CN H VIII-j-12

—Ph —OPh H VIII-j-13

—Ph —SCH₃ H VIII-j-14

—Ph —SPh H VIII-j-15

—Ph —N—Ph₂ H VIII-j-16

—Ph CH₃ H VIII-j-17

—Ph —OCH₃ H VIII-j-18

—Ph —COOH H VIII-j-19

—Ph 2-pyridyl H VIII-j-20

—Ph —Ph H VIII-j-21

—Ph H —Ph VIII-j-22

—Ph Cl H VIII-j-23

—Ph —OH H VIII-j-24

—Ph —NO₂ H VIII-j-25

—Ph —CN H VIII-j-26

—Ph —OPh H VIII-j-27

—Ph —SCH₃ H VIII-j-28

—Ph —SPh H VIII-j-29

—Ph —N—Ph₂ H VIII-j-30

—Ph CH₃ H VIII-j-31

—Ph —OCH₃ H VIII-j-32

—Ph —COOH H VIII-j-33

—Ph 2-pyridyl H VIII-j-34

—Ph —Ph H VIII-j-35

—Ph H —Ph VIII-j-36

—Ph Cl H VIII-j-37

—Ph —OH H VIII-j-38

—Ph —NO₂ H VIII-j-39

—Ph —CN H VIII-j-40

—Ph —OPh H VIII-j-41

—Ph —SCH₃ H VIII-j-42

—Ph —SPh H VIII-j-43

—Ph —N—Ph₂ H VIII-j-44

—Ph CH₃ H VIII-j-45

—Ph —OCH₃ H VIII-j-46

—Ph —COOH H VIII-j-47

—Ph 2-pyridyl H Formula (VIII) Compound No. L₁₁₂ A₁₃ ═A₂₃═A₃₃ A₁₇═A₂₇═A₃₇ A₁₈ ═A₂₈═A₃₈ VIII-k-1

H H H VIII-k-2

—Ph H H VIII-k-3

H H h VIII-k-4

—Ph H H VIII-k-5

H H H VIII-k-6

—Ph H H VIII-k-7

H A₁₇ and A₁₈ form a benzene ring. A₂₇ and A₂₈ form a benzene ring. A₃₇and A₃₈ form a benzene ring. VIII-k-8

—Ph A₁₇ and A₁₈ form a benzene ring. A₂₇ and A₂₈ form a benzene ring.A₃₇ and A₃₈ form a benzene ring. VIII-k-9

H A₁₇ and A₁₈ form a benzene ring. A₂₇ and A₂₈ form a benzene ring. A₃₇and A₃₈ form a benzene ring. VIII-k-10

—Ph A₁₇ and A₁₈ form a benzene ring. A₂₇ and A₂₈ form a benzene ring.A₃₇ and A₃₈ form a benzene ring. VIII-k-11

H A₁₇ and A₁₈ form a benzene ring. A₂₇ and A₂₈ form a benzene ring. A₃₇and A₃₈ form a benzene ring. VIII-k-12

—Ph A₁₇ and A₁₈ form a benzene ring. A₂₇ and A₂₈ form a benzene ring.A₃₇ and A₃₈ form a benzene ring. VIII-k-13

—Ph —Ph H VIII-k-14

—Ph H —Ph VIII-k-15

—Ph Cl H VIII-k-16

—Ph —OH H VIII-k-17

—Ph —NO₂ H VIII-k-18

—Ph —CN H VIII-k-19

—Ph —OPh H VIII-k-20

—Ph —SCH₃ H VIII-k-21

—Ph —SPh H VIII-k-22

—Ph —N—Ph₂ H VIII-k-23

—Ph CH₃ H VIII-k-24

—Ph —OCH₃ H VIII-k-25

—Ph —COOH H VIII-k-26

—Ph 2-pyridyl H VIII-k-27

—Ph —Ph H VIII-k-28

—Ph H —Ph VIII-k-29

—Ph Cl H VIII-k-30

—Ph —OH H VIII-k-31

—Ph —NO₂ H VIII-k-32

—Ph —CN H VIII-k-33

—Ph —OPh H VIII-k-34

—Ph —SCH₃ H VIII-k-35

—Ph —SPh H VIII-k-36

—Ph —N—Ph₂ H VIII-k-37

—Ph CH₃ H VIII-k-38

—Ph —OCH₃ H VIII-k-39

—Ph —COOH H VIII-k-40

—Ph 2-pyridyl H VIII-k-41

—Ph —Ph H VIII-k-42

—Ph H —Ph VIII-k-43

—Ph Cl H VIII-k-44

—Ph —OH H VIII-k-45

—Ph —NO₂ H VIII-k-46

—Ph —CN H VIII-k-47

—Ph —OPh H VIII-k-48

—Ph —SCH₃ H VIII-k-49

—Ph —SPh H VIII-k-50

—Ph —N—Ph₂ H VIII-k-51

—Ph CH₃ H VIII-k-52

—Ph —OCH₃ H VIII-k-53

—Ph —COOH H VIII-k-54

—Ph 2-pyridyl H Formula (VIII) Compound No. L₁₁₂ A₁₃ ═A₂₃═A₃₃ A₁₅═A₂₅═A₃₅ A₁₈ ═A₂₈═A₃₈ VIII-l-1

H H H VIII-l-2

—Ph H H VIII-l-3

H H H VIII-l-4

—Ph H H VIII-l-5

H H H VIII-l-6

—Ph —Ph H VIII-l-7

—Ph H —Ph VIII-l-8

—Ph Cl H VIII-l-9

—Ph —OH H VIII-l-10

—Ph —NO₂ H VIII-l-11

—Ph —CN H VIII-l-12

—Ph —OPh H VIIl-l-13

—Ph —SCH₃ H VIII-l-14

—Ph —SPh H VIII-l-15

—Ph —N—Ph₂ H VIII-l-16

—Ph CH₃ H VIII-l-17

—Ph —OCH₃ H VIII-l-18

—Ph —COOH H VIII-l-19

—Ph 2-pyridyl H VIII-l-20

—Ph —Ph H VIII-l-21

—Ph H —Ph VIII-l-22

—Ph Cl H VIII-l-23

—Ph —OH H VIII-l-24

—Ph —NO₂ H VIII-l-25

—Ph —CN H VIII-l-26

—Ph —OPh H VIII-l-27

—Ph —SCH₃ H VIII-l-28

—Ph —SPh H VIII-l-29

—Ph —N—Ph₂ H VIII-l-30

—Ph CH₃ H VIII-l-31

—Ph —OCH₃ H VIII-l-32

—Ph —COOH H VIII-l-33

—Ph 2-pyridyl H VIII-l-34

—Ph —Ph H VIII-l-35

—Ph H —Ph VIII-l-36

—Ph Cl H VIII-l-37

—Ph —OH H VIII-l-38

—Ph —NO₂ H VIII-l-39

—Ph —CN H VIII-l-40

—Ph —OPh H VIII-l-41

—Ph —SCH₃ H VIII-l-42

—Ph —SPh H VIII-l-43

—Ph —N—Ph₂ H VIII-l-44

—Ph CH₃ H VIII-l-45

—Ph —OCH₃ H VIII-l-46

—Ph —COOH H VIII-l-47

—Ph 2-pyridyl H Formula (VIII) Compound No. L₁₁₁ A₁₂═A₂₂ A₁₃═A₂₃ A₁₅═A₂₅A₁₇═A₂₇ A₁₈═A₂₈ VIII-m-1 single bond H H H H H VIII-m-2 single bond H HCH₃ H H VIII-m-3 single bond H H H CH₃ H VIII-m-4 single bond H H H HCH₃ VIII-m-5 single bond H H H n-C₂H₅ H VIII-m-6 single bond H H Hn-C₃H₇ H VIII-m-7 single bond H H H n-C₄H₉ H VIII-m-8 single bond H H Ht-C₄H₉ H VIII-m-9 single bond H H Ph H H VIII-m-10 single bond H H H PhH VIII-m-11 single bond H H H H Ph VIII-m-12 single bond H H H1-naphthyl H VIII-m-13 single bond H H H 2-naphthyl H VIII-m-14 singlebond H H H 4-biphenylyl H VIII-m-15 single bond H H H 3-biphenylyl HVIII-m-16 single bond H H H 2-biphenylyl H VIII-m-17 single bond H H H2-biphenylyl H VIII-m-18 single bond Ph Ph H H H VIII-m-19 single bondPh Ph CH₃ H H VIII-m-20 single bond Ph Ph H CH₃ H VIII-m-21 single bondPh Ph H H CH₃ VIII-m-22 single bond Ph Ph H n- C₂H₅ H VIII-m-23 singlebond Ph Ph H n-C₃H₇ H VIII-m-24 single bond Ph Ph H n-C₄H₉ H VIII-m-25single bond Ph Ph H t-C₄H₉ H VIII-m-26 single bond Ph Ph Ph H HVIII-m-27 single bond Ph Ph H Ph H VIII-m-28 single bond Ph Ph H H PhVIII-m-29 single bond Ph Ph H 1-naphthyl H VIII-m-30 single bond Ph Ph H2-naphthyl H VIII-m-31 single bond Ph Ph H 4-biphenylyl H VIII-m-32single bond Ph Ph H 3-biphenylyl H VIII-m-33 single bond Ph Ph H2-biphenylyl H VIII-m-34 single bond

H H H VIII-m-35 single bond

CH₃ H H VIII-m-36 single bond

H CH₃ H VIII-m-37 single bond

H H CH₃ VIII-m-38 single bond

H n-C₂H₅ H VIII-m-39 single bond

H n-C₃H₇ H VIII-m-40 single bond

H n-C₄H₉ H VIII-m-41 single bond

H t-C₄H₉ H VIII-m-42 single bond

—Ph H H VIII-m-43 single bond

H —Ph H VIII-m-44 single bond

H H Ph VIII-m-45 single bond

H 1-naphthyl H VIII-m-46 single bond

H 2-naphthyl H VIII-m-47 single bond

H 4-biphenylyl H VIII-m-48 single bond

H 3-biphenylyl H VIII-m-49 single bond

H 2-biphenylyl H VIII-m-50

H H H H H VIII-m-51

H H CH₃ H H VIII-m-52

H H H CH₃ H VIII-m-53

H H H H CH₃ VIII-m-54

H H H n-C₂H₅ H VIII-m-55

H H H n-C₃H₇ H VIII-m-56

H H H n-C₄H₉ H VIII-m-57

H H H t-C₄H₉ H VIII-m-58

H H Ph H H VIII-m-59

H H H Ph H VIII-m-60

H H H H Ph VIII-m-61

H H H 1-naphthyl H VIII-m-62

H H H 2-naphthyl H VIII-m-63

H H H 4-biphenylyl H VIII-m-64

H H H 3-biphenylyl H VIII-m-65

H H H 2-biphenylyl H VIII-m-66

H H H 2-biphenylyl H VIII-m-67

Ph Ph H H H VIII-m-68

Ph Ph CH₃ H H VIII-m-69

Ph Ph H CH₃ H VIII-m-70

Ph Ph H H CH₃ VIII-m-71

Ph Ph H n-C₂H₅ H VIII-m-72

Ph Ph H n-C₃H₇ H VIII-m-73

Ph Ph H n-C₄H₉ H VIII-m-74

Ph Ph H t-C₄H₉ H VIII-m-75

Ph Ph Ph H H VIII-m-76

Ph Ph H Ph H VIII-m-77

Ph Ph H H Ph VIII-m-78

Ph Ph H 1-naphthyl H VIII-m-79

Ph Ph H 2-naphthyl H VIII-m-80

Ph Ph H 4-biphenylyl H VIII-m-81

Ph Ph H 3-biphenylyl H VIII-m-82

Ph Ph H 2-biphenylyl H VIII-m-83

H H H VIII-m-84

CH₃ H H VIII-m-85

H CH₃ H VIII-m-86

H H CH₃ VIII-m-87

H n-C₂H₅ H VIII-m-88

H n-C₃H₇ H VIII-m-89

H n-C₄H₉ H VIII-m-90

H t-C₄H₉ H VIII-m-91

Ph H H VIII-m-92

H Ph H VIII-m-93

H H Ph VIII-m-94

H 1-naphthyl H VIII-m-95

H 2-naphthyl H VIII-m-96

H 4-biphenylyl H VIII-m-97

H 3-biphenylyl H VIII-m-98

H 2-biphenylyl H VIII-m-99

H H H H H VIII-m-100

H H CH₃ H H VIII-m-101

H H H CH₃ H VIII-m-102

H H H H CH₃ VIII-m-103

H H H n-C₂H₅ H VIII-m-104

H H H n-C₃H₇ H VIII-m-105

H H H n-C₄H₉ H VIII-m-106

H H H t-C₄H₉ H VIII-m-107

H H Ph H H VIII-m-108

H H H Ph H VIII-m-109

H H H H Ph VIII-m-110

H H H 1-naphthyl H VIII-m-111

H H H 2-naplithyl H VIII-m-112

H H H 4-biphenylyl H VIII-m-113

H H H 3-biphenylyl H VIII-m-114

H H H 2-biphenylyl H VIII-m-115

H H H 2-biphenylyl H VIII-m-116

Ph Ph H H H VIII-m-117

Ph Ph CH₃ H H VIII-m-118

Ph Ph H CH₃ H VIII-m-119

Ph Ph H H CH₃ VIII-m-120

Ph Ph H n-C₂H₅ H VIII-m-121

Ph Ph H n-C₃H₇ H VIII-m-122

Ph Ph H n-C₄H₉ H VIII-m-123

Ph Ph H t-C₄H₉ H VIII-m-124

Ph Ph Ph H H VIII-m-125

Ph Ph H Ph H VIII-m-126

Ph Ph H H Ph VIII-m-127

Ph Ph H 1-naphthyl H VIII-m-128

Ph Ph H 2-naphthyl H VIII-m-129

Ph Ph H 4-biphenylyl H VIII-m-130

Ph Ph H 3-biphenylyl H VIII-m-131

Ph Ph H 2-biphenylyl H VIII-m-132

H H H VIII-m-133

CH₃ H H VIII-m-134

H CH₃ H VIII-m-135

H H CH₃ VIII-m-136

H n-C₂H₅ H VIII-m-137

H n-C₃H₇ H VIII-m-138

H n-C₄H₉ H VIII-m-139

H t-C₄H₉ H VIII-m-140

Ph H H VIII-m-141

H Ph H VIII-m-142

H H Ph VIII-m-143

H 1-naphthyl H VIII-m-144

H 2-naphthyl H VIII-m-145

H 4-biphenylyl H VIII-m-146

H 3-biphenylyl H VIII-m-147

H 3-biphenylyl H

[0263] These quinoxaline compounds are obtained by (i) a processinvolving condensing diaminobenzene or derivatives thereof,diaminopyridine or derivatives thereof, diaminopyrimidine or derivativesthereof, diaminopyridazine or derivatives thereof with a halogenateddiketone compound, followed by coupling using a nickel complex of1,5-cyclooctadiene or the like, (ii) condensing diaminobenzene orderivatives thereof, diaminopyridine or derivatives thereof,diaminopyrimidine or derivatives thereof, diaminopyridazine orderivatives thereof with a bisdiketone compound, (iii) condensing abisdiamine compound with a diketone compound, or (iv) converting astarting compound into an organometallic reagent of tin or the like,followed by cross-coupling.

[0264] These compounds can be identified by elemental analysis, massanalysis, IR spectroscopy, ¹H and ¹³C NMR, etc.

[0265] In general, the quinoxaline compounds have a molecular weight ofabout 500 to about 2,000, a melting point of about 250 to about 500° C.,and a glass transition temperature (Tg) of about 90 to about 200° C. Byconventional vacuum deposition or the like, they form a transparent,smooth film of quality which maintains a stable amorphous state evenabove room temperature and over a long period of time.

[0266] The term “host material” used herein means a material whichparticipates in light emission, but does not emit light by itself oremits light at a very low luminance. Specifically, an appropriatedifference in luminance between the host and the dopant is such that themaximum luminance of the host is equal to or less than 10%, especiallyequal to or less than 2% of the maximum luminance of the dopant.

[0267] Dopants

[0268] A class of organic compounds useful as the dopant according tothe invention are compounds of the following formula (V).

[0269] Herein X₁ to X₁₀, L₁ and L₂ are independently hydrogen, halogenatoms, straight, branched or cyclic alkyl radicals which may havesubstituents, straight, branched or cyclic alkoxy radicals which mayhave substituents, straight, branched or cyclic alkylthio radicals whichmay have substituents, straight, branched or cyclic alkenyl radicalswhich may have substituents, straight, branched or cyclic alkenyloxyradicals which may have substituents, straight, branched or cyclicalkenylthio radicals which may have substituents, substituted orunsubstituted aralkyl radicals, substituted or unsubstituted aralkyloxyradicals, substituted or unsubstituted aralkylthio radicals, substitutedor unsubstituted aryl radicals, substituted or unsubstituted aryloxyradicals, substituted or unsubstituted arylthio radicals, substituted orunsubstituted amino radicals, cyano, hydroxyl, —COOR¹ radicals (whereinR¹ is hydrogen, a substituted or unsubstituted straight, branched orcyclic alkyl radical, a substituted or unsubstituted straight, branchedor cyclic alkenyl radical, a substituted or unsubstituted aralkylradical or a substituted or unsubstituted aryl radical), —COR² radicals(wherein R² is hydrogen, a substituted or unsubstituted straight,branched or cyclic alkyl radical, a substituted or unsubstitutedstraight, branched or cyclic alkenyl radical, a substituted orunsubstituted aralkyl radical, a substituted or unsubstituted arylradical or an amino radical), or —OCOR³ radicals (wherein R³ is asubstituted or unsubstituted straight, branched or cyclic alkyl radical,a substituted or unsubstituted straight, branched or cyclic alkenylradical, a substituted or unsubstituted aralkyl radical, or asubstituted or unsubstituted aryl radical), or at least two adjoininggroups selected from X₁ to X₁₀, L₁ and L₂ may bond or fuse together toform a substituted or unsubstituted carbocyclic aliphatic ring, aromaticring or fused aromatic ring with the carbon atoms to which they areattached, or L₁ and L₂ each may be a single bond.

[0270] Preferably, at least two adjoining groups selected from X₁ toX₁₀, L₁ and L₂ bond or fuse together to form a substituted orunsubstituted carbocyclic aliphatic ring, aromatic ring or fusedaromatic ring with the carbon atoms to which they are attached. L₁ andL₂ each may be a single bond. n is 1 or 2.

[0271] Of the compounds of formula (V), preferred arediindeno[1,2,3-cd:1′,2′,3′-lm]perylene derivatives, having a skeleton ofthe following formula (VI).

[0272] In formula (VI), X₁ to X₆, X₉ to X₁₀, X₁₁ to X₁₆, X₁₉ and X₂₀ areindependently hydrogen, halogen atoms, straight, branched or cyclicalkyl radicals which may have substituents, straight, branched or cyclicalkoxy radicals which may have substituents, straight, branched orcyclic alkylthio radicals which may have substituents, straight,branched or cyclic alkenyl radicals which may have substituents,straight, branched or cyclic alkenyloxy radicals which may havesubstituents, straight, branched or cyclic alkenylthio radicals whichmay have substituents, substituted or unsubstituted aralkyl radicals,substituted or unsubstituted aralkyloxy radicals, substituted orunsubstituted aralkylthio radicals, substituted or unsubstituted arylradicals, substituted or unsubstituted aryloxy radicals, substituted orunsubstituted arylthio radicals, substituted or unsubstitutedarylalkenyl radicals, substituted or unsubstituted alkenylaryl radicals,substituted or unsubstituted amino radicals, cyano, hydroxyl, —COOR¹radicals (wherein R¹ is hydrogen, a substituted or unsubstitutedstraight, branched or cyclic alkyl radical, a substituted orunsubstituted straight, branched or cyclic alkenyl radical, asubstituted or unsubstituted aralkyl radical or a substituted orunsubstituted aryl radical), —COR² radicals (wherein R² is hydrogen, asubstituted or unsubstituted straight, branched or cyclic alkyl radical,a substituted or unsubstituted straight, branched or cyclic alkenylradical, a substituted or unsubstituted aralkyl radical, a substitutedor unsubstituted aryl radical or an amino radical), or —OCOR³ radicals(wherein R³ is a substituted or unsubstituted straight, branched orcyclic alkyl radical, a substituted or unsubstituted straight, branchedor cyclic alkenyl radical, a substituted or unsubstituted aralkylradical, or a substituted or unsubstituted aryl radical), or at leasttwo adjoining groups selected from X₁ to X₂₀ may bond together to form asubstituted or unsubstituted carbocyclic aliphatic ring, aromatic ringor fused aromatic ring with the carbon atoms to which they are attached.

[0273] The term “aryl radicals” is used herein to encompass carbocyclicaromatic radicals such as phenyl and naphthyl and heterocyclic aromaticradicals such as furyl, thienyl and pyridyl.

[0274] The straight, branched or cyclic alkyl radicals, straight,branched or cyclic alkoxy radicals, straight, branched or cyclicalkylthio radicals, straight, branched or cyclic alkenyl radicals,straight, branched or cyclic alkenyloxy radicals, and straight, branchedor cyclic alkenylthio radicals, represented by X₁ to X₂₀ in formulas (V)and (VI), may have a substituent or substituents, for example, halogenatoms, aryl groups of 4 to 20 carbon atoms, alkoxy groups of 1 to 20carbon atoms, alkoxyalkoxy groups of 2 to 20 carbon atoms, alkenyloxygroups of 2 to 20 carbon atoms, aralkyloxy groups of 4 to 20 carbonatoms, aralkyloxyalkoxy groups of 5 to 20 carbon atoms, aryloxy groupsof 3 to 20 carbon atoms, aryloxyalkoxy groups of 4 to 20 carbon atoms,arylalkenyl groups of 5 to 20 carbon atoms, aralkylalkenyl groups of 6to 20 carbon atoms, alkylthio groups of 1 to 20 carbon atoms,alkoxyalkylthio groups of 2 to 20 carbon atoms, alkylthioalkylthiogroups of 2 to 20 carbon atoms, alkenylthio groups of 2 to 20 carbonatoms, aralkylthio groups of 4 to 20 carbon atoms, aralkyloxyalkylthiogroups of 5 to 20 carbon atoms, aralkylthioalkylthio groups of 5 to 20carbon atoms, arylthio groups of 3 to 20 carbon atoms, aryloxyalkylthiogroups of 4 to 20 carbon atoms, arylthioalkylthio groups of 4 to 20carbon atoms, and heteroatom-containing cyclic alkyl groups of 4 to 20carbon atoms. The aryl groups included in these substituents may befurther substituted with halogen atoms, alkyl groups of 1 to 10 carbonatoms, alkoxy groups of 1 to 10 carbon atoms, aryl groups of 3 to 10carbon atoms, and aralkyl groups of 4 to 10 carbon atoms, among others.

[0275] The aralkyl radicals, aralkyloxy radicals, aralkylthio radicals,aryl radicals, aryloxy radicals and arylthio radicals, represented by X₁to X₂₀ in formulas (V) and (VI), may have a substituent or substituents,for example, alkyl groups of 1 to 20 carbon atoms, alkenyl groups of 2to 20 carbon atoms, aralkyl groups of 4 to 20 carbon atoms, aryl groupsof 3 to 20 carbon atoms, alkoxy groups of 1 to 20 carbon atoms,alkoxyalkyl groups of 2 to 20 carbon atoms, alkoxyalkyloxy groups of 2to 20 carbon atoms, alkenyloxy groups of 2 to 20 carbon atoms,alkenyloxyalkyl groups of 3 to 20 carbon atoms, alkenyloxyalkyloxygroups of 3 to 20 carbon atoms, aralkyloxy groups of 4 to 20 carbonatoms, aralkyloxyalkyl groups of 5 to 20 carbon atoms,aralkyloxyalkyloxy groups of 5 to 20 carbon atoms, aryloxy groups of 3to 20 carbon atoms, aryloxyalkyl groups of 4 to 20 carbon atoms,aryloxyalkyloxy groups of 4 to 20 carbon atoms, alkylcarbonyl groups of2 to 20 carbon atoms, alkenylcarbonyl groups of 3 to 20 carbon atoms,aralkylcarbonyl groups of 5 to 20 carbon atoms, arylcarbonyl groups of 4to 20 carbon atoms, alkoxycarbonyl groups of 2 to 20 carbon atoms,alkenyloxycarbonyl groups of 3 to 20 carbon atoms, aralkyloxycarbonylgroups of 5 to 20 carbon atoms, aryloxycarbonyl groups of 4 to 20 carbonatoms, alkylcarbonyloxy groups of 2 to 20 carbon atoms,alkenylcarbonyloxy groups of 3 to 20 carbon atoms, aralkylcarbonyloxygroups of 5 to 20 carbon atoms, arylcarbonyloxy groups of 4 to 20 carbonatoms, alkylthio groups of 1 to 20 carbon atoms, aralkylthio groups of 4to 20 carbon atoms, arylthio groups of 3 to 20 carbon atoms, nitro,cyano, formyl, halogen atoms, halogenated alkyl, hydroxyl, amino,N-mono-substituted amino groups of 1 to 20 carbon atoms, andN,N-di-substituted amino groups of 2 to 40 carbon atoms. The aryl groupsincluded in these substituents may be further substituted with halogenatoms, alkyl groups of 1 to 10 carbon atoms, alkoxy groups of 1 to 10carbon atoms, aryl groups of 6 to 10 carbon atoms, and aralkyl groups of7 to 10 carbon atoms, among others.

[0276] The amino radicals represented by X₁ to X₂₀ in formulas (V) and(VI) may have a substituent or substituents, for example, be mono- ordi-substituted with alkyl groups of 1 to 20 carbon atoms, aralkyl groupsof 4 to 20 carbon atoms, and aryl groups of 3 to 20 carbon atoms.

[0277] The alkyl, alkenyl, aralkyl and aryl radicals represented by R¹,R² and R³ in formulas (V) and (VI) may have a substituent orsubstituents, as exemplified for X₁ to X₂₀.

[0278] In a preferred embodiment, X₅, X₆, X₉, X₁₀, X₁₅, X₁₆, X₁₉ and X₂₀are hydrogen, and X₁ to X₄ and X₁₁ to X₁₄ are independently hydrogen,halogen atoms, straight, branched or cyclic alkyl radicals of 1 to 24carbon atoms in total which may have substituents, straight, branched orcyclic alkoxy radicals of 1 to 24 carbon atoms in total which may havesubstituents, straight, branched or cyclic alkenyl, alkenylaryl andarylalkenyl radicals of 2 to 24 carbon atoms in total which may havesubstituents, substituted or unsubstituted aralkyl groups of 7 to 24carbon atoms in total, substituted or unsubstituted aryl radicals of 6to 24 carbon atoms in total, cyano radicals, heterocyclic radicals,hydroxyl radicals, —COOR¹, —COR² or —OCOR³ radicals wherein R¹, R² andR³ are as defined above.

[0279] Two adjoining groups selected from X₁ to X₂₀ may bond or fusetogether to form a substituted or unsubstituted carbocyclic aliphaticring, aromatic ring or fused aromatic ring with the carbon atoms towhich they are attached.

[0280] The organic EL device of the invention is characterized by theinclusion of at least one fluoranthene derivative ordiindeno[1,2,3-cd:1′,2′,3′-lm]perylene derivative. The use of adiindeno[1,2,3-cd:1′,2′,3′-lm]perylene derivative in a light emittinglayer as a luminescent component, for example, enables to produce anorganic EL device having improved luminance and durability over similarEL devices of the prior art. The use of the specific derivative incombination with another luminescent component to form a light emittinglayer enables to produce an organic EL device capable of emitting whitelight and having improved luminance and durability.

[0281] Illustrative, non-limiting, examples of the compounds of formulas(V) and (VI) according to the invention are given below. Ph designatesphenyl. +TC,51/

“A and B form a fused ring” in

means

Com- pound No. X1 X2 X3 X6 X7 X8 A-1 H H H H H H A-2 H H H H H H A-3 H HH H H H A-4 H H H H H H A-5 H H H H H H A-6 H H H H H H A-7 H H H H H HA-8 H H H H H H A-9 H H H H H H A-10 H H H H H H A-11 Ph H H H H Ph A-12

H H H H

A-13 CH3 H H H H CH3 A-14 H Ph H H Ph H A-15 H

H H

H A-16 H CH3 H H CH3 H A-17 X1 and X2 form a fused ring. H H H H A-18 X1and X2 form a fused ring. H H H H A-19 X1 and X2 form a fused ring. H HH H A-20 X1 and X2 form a fused ring. H H H H A-21 X1 and X2 form afused ring. H H H H A-22 X1 and X2 form a fused ring. H H H H A-23 X1and X2 form a fused ring. H H H H A-24 X1 and X2 form a fused ring. H HH H A-25 X1 and X2 form a fused ring. H H H H A-26 X1 and X2 form afused ring. H H H H A-27 X1 and X2 form a fused ring. H H H Ph A-28 X1and X2 form a fused ring. H H H

A-29 X1 and X2 form a fused ring. H H H CH3 A-30 X1 and X2 form a fusedring. H H Ph H A-31 X1 and X2 form a fused ring. H H

H A-32 X1 and X2 form a fused ring. H H CH3 H A-33 H H H H H H A-34 H HH H H H A-35 H H H H H H A-36 H H H H H H A-37 H H H H H H A-38 H H H HH H A-39 H H H H H H A-40 H H H H H H A-41 H H H H H H A-42 H H H H H HA-43 Ph H H H H Ph A-44

H H H H

A-45 CH3 H H H H CH3 A-46 H Ph H H Ph H A-47 H

H H

H A-48 CH3 H H CH3 H A-49 H H H H H H A-50 Ph H H H H Ph A-51

H H H H

A-52 CH3 H H H H CH3 A-53 H Ph H H Ph H A-54 H

H H

H A-55 H CH3 H H CH3 H A-56 X1 and X2 form a fused ring. H H X1 and X2form a fused ring. A-57 X1 and X2 form a fused ring. H H X1 and X2 forma fused ring. A-58 X1 and X2 form a fused ring. H H X1 and X2 form afused ring. A-59 X1 and X2 form a fused ring. H H X1 and X2 form a fusedring. A-60 X1 and X2 form a fused ring. H H X1 and X2 form a fused ring.A-61 X1 and X2 form a fused ring. H H X1 and X2 form a fused ring. A-62X1 and X2 form a fused ring. H H X1 and X2 form a fused ring. A-63 X1and X2 form a fused ring. H H X1 and X2 form a fused ring. A-64 X1 andX2 form a fused ring. H H X1 and X2 form a fused ring. A-65 X1 and X2form a fused ring. H H X1 and X2 form a fused ring. A-66 X1 and X2 forma fused ring. H H X1 and X2 form a fused ring. Com- pound No. X11 X12X13 X14 A-1 H H H H A-2 Ph H H Ph A-3

H H

A-4

H H

A-5

H H

A-6 CH3 H H CH3 A-7

H H

A-8 Ph Ph Ph Ph A-9 Ph

Ph A-10 Ph CH3 CH3 Ph A-11 Ph H H Ph A-12 Ph H H Ph A-13 Ph H H Ph A-14Ph H H Ph A-15 Ph H H Ph A-16 Ph H H Ph A-17 H H H H A-18 Ph H H Ph A-19

H H

A-20

H H

A-21

H H

A-22 CH3 H H CH3 A-23

H H

A-24 Ph Ph Ph Ph A-25 Ph

Ph A-26 Ph CH3 CH3 Ph A-27 Ph H H Ph A-28 Ph H H Ph A-29 Ph H H Ph A-30Ph H H Ph A-31 Ph H H Ph A-32 Ph H H Ph A-33 H H X13 and X14 form afused ring. A-34 Ph H X13 and X14 form a fused ring. A-35

H X13 and X14 form a fused ring. A-36

H X13 and X14 form a fused ring. A-37

H X13 and X14 form a fused ring. A-38 CH3 H X13 and X14 form a fusedring. A-39

H X13 and X14 form a fused ring. A-40 Ph Ph X13 and X14 form a fusedring. A-41 Ph

X13 and X14 form a fused ring. A-42 Ph CH3 X13 and X14 form a fusedring. A-43 Ph H X13 and X14 form a fused ring. A-44 Ph H X13 and X14form a fused ring. A-45 Ph H X13 and X14 form a fused ring. A-46 Ph HX13 and X14 form a fused ring. A-47 Ph H X13 and X14 form a fused ring.A-48 Ph H X13 and X14 form a fused ring. A-49 X13 and X14 form a fusedring. X13 and X14 form a fused ring. A-50 X13 and X14 form a fused ring.X13 and X14 form a fused ring. A-51 X13 and X14 form a fused ring. X13and X14 form a fused ring. A-52 X13 and X14 form a fused ring. X13 andX14 form a fused ring. A-53 X13 and X14 form a fused ring. X13 and X14form a fused ring. A-54 X13 and X14 form a fused ring. X13 and X14 forma fused ring. A-55 X13 and X14 form a fused ring. X13 and X14 form afused ring. A-56 H H H H A-57 Ph H H Ph A-58

H H

A-59

H H

A-60

H H

A-61 CH3 H H CH3 A-62

H H

A-63 Ph Ph Ph Ph A-64 Ph

Ph A-65 Ph CH3 CH3 Ph A-66 Ph H H Ph

[0282]

“A and B form a fused ring in

means

Compound No. X1 X2 X3 X6 X7 X8 X11 B-1 H H H H H H H B-2 H H H H H H PhB-3 H H H H H H

B-4 H H H H H H

B-5 H H H H H H

B-6 H H H H H H CH3 B-7 H H H H H H

B-8

H H H H

Ph B-9 CH3 H H H H CH3 Ph B-10 H Ph H H Ph H Ph B-11 H

H H

H Ph B-12 H CH3 H H CH3 H Ph B-13 H H H H X7 and X8 form a fused ring. HB-14 H H H H X7 and X8 form a fused ring. Ph B-15 H H H H X7 and X8 forma fused ring.

B-16 H H H H X7 and X8 form a fused ring.

B-17 H H H H X7 and X8 form a fused ring.

B-18 H H H H X7 and X8 form a fused ring. CH3 B-19 H H H H X7 and X8form a fused ring.

B-20 H H H H X7 and X8 form a fused ring. Ph B-21 H H H H X7 and X8 forma fused ring. Ph B-22 H H H H X7 and X8 form a fused ring. Ph B-23 H H HH X7 and X8 form a fused ring. Ph B-24 H H H H X7 and X8 form a fusedring. Ph B-25 H H H H X7 and X8 form a fused ring. Ph B-26 H H H H X7and X8 form a fused ring. Ph B-27 H H H H X7 and X8 form a fused ring.Ph B-28 H H H H X7 and X8 form a fused ring. Ph B-29 Ph H H H X7 and X8form a fused ring. Ph B-30

H H H X7 and X8 form a fused ring. Ph B-31 CH3 H H H X7 and X8 form afused ring. Ph B-32 H H H H H H H B-33 H H H H H H Ph B-34 H H H H H H

B-35 H H H H H H

B-36 H H H H H H

B-37 H H H H H H CH3 B-38 H H H H H H

B-39 H H H H H H Ph B-40 H H H H H H Ph B-41 H H H H H H Ph B-42 H H H HH H Ph B-43 H H H H H H Ph B-44 H H H H H H Ph B-45 H H H H H H Ph B-46H H H H H H Ph B-47 H H H H H H Ph B-48 Ph H H H H Ph Ph B-49

H H H H

Ph B-50 CH3 H H H H CH3 Ph B-51 H Ph H H Ph H Ph B-52 H

H H

H Ph B-53 H CH3 H H CH3 H Ph B-54 H H H H H H H B-55 H H H H H H Ph B-56H H H H H H

B-57 H H H H H H

B-58 H H H H H H

B-59 H H H H H H CH3 B-60 H H H H H H

B-61 H H H H H H Ph B-62 H H H H H H Ph B-63 H H H H H H Ph B-64 H H H HH H Ph B-65 H H H H H H Ph B-66 H H H H H H Ph B-67 H H H H H H Ph B-68H H H H H H Ph B-69 H H H H H H Ph B-70 Ph H H H H Ph Ph B-71

H H H H

Ph B-72 CH3 H H H H CH3 Ph B-73 H Ph H H Ph H Ph B-74 H

H H

H Ph B-75 H CH3 H H CH3 H Ph B-76 X1 and X2 form a fused ring. H H X7and X8 form a fused ring. H B-77 X1 and X2 form a fused ring. H H X7 andX8 form a fused ring. Ph B-78 X1 and X2 form a fused ring. H H X7 and X8form a fused ring.

B-79 X1 and X2 form a fused ring. H H X7 and X8 form a fused ring.

B-80 X1 and X2 form a fused ring. H H X7 and X8 form a fused ring.

B-81 X1 and X2 form a fused ring. H H X7 and X8 form a fused ring. CH3B-82 X1 and X2 form a fused ring. H H X7 and X8 form a fused ring.

B-83 X1 and X2 form a fused ring. H H X7 and X8 form a fused ring. PhB-84 X1 and X2 form a fused ring. H H X7 and X8 form a fused ring. PhB-85 X1 and X2 form a fused ring. H H X7 and X8 form a fused ring. PhB-86 X1 and X2 form a fused ring. H H X7 and X8 form a fused ring. PhB-87 X1 and X2 form a fused ring. H H X7 and X8 form a fused ring. PhB-88 X1 and X2 form a fused ring. H H X7 and X8 form a fused ring. PhB-89 X1 and X2 form a fused ring. H H X7 and X8 form a fused ring. PhB-90 X1 and X2 form a fused ring. H H X7 and X8 form a fused ring. PhB-91 X1 and X2 form a fused ring. H H X7 and X8 form a fused ring. PhCompound No. X14 X15 X16 X17 X18 B-1 H X15 and X16 form a fused ring.X17 and X18 form a fused ring. B-2 Ph X15 and X16 form a fused ring. X17and X18 form a fused ring. B-3

X15 and X16 form a fused ring. X17 and X18 form a fused ring. B-4

X15 and X16 form a fused ring. X17 and X18 form a fused ring. B-5

X15 and X16 form a fused ring. X17 and X18 form a fused ring. B-6 CH3X15 and X16 form a fused ring. X17 and X18 form a fused ring. B-7

X15 and X16 form a fused ring. X17 and X18 form a fused ring. B-8 Ph X15and X16 form a fused ring. X17 and X18 form a fused ring. B-9 Ph X15 andX16 form a fused ring. X17 and X18 form a fused ring. B-10 Ph X15 andX16 form a fused ring. X17 and X18 form a fused ring. B-11 Ph X15 andX16 form a fused ring. X17 and X18 form a fused ring. B-12 Ph X15 andX16 form a fused ring. X17 and X18 form a fused ring. B-13 H H H H HB-14 Ph H H H H B-15

H H H H B-16

H H H H B-17

H H H H B-18 CH3 H H H H B-19

H H H H B-20 Ph Ph H H Ph B-21 Ph

H H

B-22 Ph

H H

B-23 Ph

H H

B-24 Ph CH3 H H CH3 B-25 Ph

H H

B-26 Ph H Ph Ph H B-27 Ph H

H B-28 Ph H CH3 CH3 H B-29 Ph H H H H B-30 Ph H H H H B-31 Ph H H H HB-32 H X15 and X16 form a fused ring. H H B-33 Ph X15 and X16 form afused ring. H H B-34

X15 and X16 form a fused ring. H H B-35

X15 and X16 form a fused ring. H H B-36

X15 and X16 form a fused ring. H H B-37 CH3 X15 and X16 form a fusedring. H H B-38

X15 and X16 form a fused ring. H H B-39 Ph X15 and X16 form a fusedring. H Ph B-40 Ph X15 and X16 form a fused ring. H

B-41 Ph X15 and X16 form a fused ring. H

B-42 Ph X15 and X16 form a fused ring. H

B-43 Ph X15 and X16 form a fused ring. H CH3 B-44 Ph X15 and X16 form afused ring. H

B-45 Ph X15 and X16 form a fused ring. Ph H B-46 Ph X15 and X16 form afused ring.

H B-47 Ph X15 and X16 form a fused ring. CH3 H B-48 Ph X15 and X16 forma fused ring. H H B-49 Ph X15 and X16 form a fused ring. H H B-50 Ph X15and X16 form a fused ring. H H B-51 Ph X15 and X16 form a fused ring. HH B-52 Ph X15 and X16 form a fused ring. H H B-53 Ph X15 and X16 form afused ring. H H B-54 H H H H H B-55 Ph H H H H B-56

H H H H B-57

H H H H B-58

H H H H B-59 CH3 H H H H B-60

H H H H B-61 Ph Ph H H Ph B-62 Ph

H H

B-63 Ph

H H

B-64 Ph

H H

B-65 Ph CH3 H H CH3 B-66 Ph

H H

B-67 Ph H Ph Ph H B-68 Ph H

H B-69 Ph H CH3 CH3 H B-70 Ph H H H H B-71 Ph H H H H B-72 Ph H H H HB-73 Ph H H H H B-74 Ph H H H H B-75 Ph H H H H B-76 H H H H H B-77 Ph HH H H B-78

H H H H B-79

H H H H B-80

H H H H B-81 CH3 H H H H B-82

H H H H B-83 Ph Ph H H Ph B-84 Ph

H H

B-85 Ph

H H

B-86 Ph

H H

B-87 Ph CH3 H H CH3 B-88 Ph

H H

B-89 Ph H Ph Ph H B-90 Ph H

H B-91 Ph H CH3 CH3 H

“C, A and B form a fused ring” in

means

Compound No. X1 X2 X8 X3 X6 X7 X11 X14 B-92 X1, X2 and X8 form a fusedring. H H H H H B-93 X1, X2 and X8 form a fused ring. H H H Ph Ph B-94X1, X2 and X8 form a fused ring. H H H

B-95 X1, X2 and X8 form a fused ring. H H H

B-96 X1, X2 and X8 form a fused ring. H H H

B-97 X1, X2 and X8 form a fused ring. H H H CH3 CH3 B-98 X1, X2 and X8form a fused ring. H H H

B-99 X1, X2 and X8 form a fused ring. H H H Ph Ph B-100 X1, X2 and X8form a fused ring. H H H Ph Ph B-101 X1, X2 and X8 form a fused ring. HH H Ph Ph B-102 X1, X2 and X8 form a fused ring. H H H Ph Ph B-103 X1,X2 and X8 form a fused ring. H H H Ph Ph B-104 X1, X2 and X8 form afused ring. H H H Ph Ph B-105 X1, X2 and X8 form a fused ring. H H H PhPh B-106 X1, X2 and X8 form a fused ring. H H H Ph Ph B-107 X1, X2 andX8 form a fused ring. H H H Ph Ph B-108 X1, X2 and X8 form a fused ring.H H Ph Ph Ph B-109 X1, X2 and X8 form a fused ring. H H

Ph Ph B-110 X1, X2 and X8 form a fused ring. H H CH3 Ph Ph Compound No.X15 X16 X17 X18 B-92 H H H H B-93 H H H H B-94 H H H H B-95 H H H H B-96H H H H B-97 H H H H B-98 H H H H B-99 Ph H H Ph B-100

H H

B-101

H H

B-102

H H

B-103 CH3 H H CH3 B-104

H H

B-105 H Ph Ph H B-106 H

H B-107 H CH3 CH3 H B-108 H H H H B-109 H H H H B-110 H H H H

[0283]

“A and B form a fused ring in

means

Com- pound No. X1 X2 X3 X6 X7 X8 C-1 H H H H H H C-2 H H H H H H C-3 H HH H H H C-4 H H H H H H C-5 H H H H H H C-6 H H H H H H C-7 H H H H H HC-8 H H H H H H C-9 H H H H H H C-10 H H H H H H C-11 Ph H H H H Ph C-12

H H H H

C-13 CH3 H H H H CH3 C-14 H Ph H H Ph H C-15 H

H H

H C-16 H CH3 H H CH3 H Com- pound No. X11 X14 P1 P2 C-1 H H H H C-2 PhPh H H C-3

H H C-4

H H C-5

H H C-6 CH3 CH3 H H C-7

H H C-8 Ph Ph Ph Ph C-9 Ph Ph

C-10 Ph Ph CH3 CH3 C-11 Ph Ph H H C-12 Ph Ph H H C-13 Ph Ph H H C-14 PhPh H H C-15 Ph Ph H H C-16 Ph Ph H H

[0284]

“A and B form a fused ring” in

means

Compound No. X1 X2 X3 X4 X5 X6 X7 X8 X11 X14 D-1 H H H H H H H H H H D-2H H H H H H H H Ph Ph D-3 H H H H H H H H

D-4 H H H H H H H H

D-5 H H H H H H H H CH3 CH3 D-6 H H H H H H H H

D-7 H H H H H H H H

D-8 H H H H H H H H Ph Ph D-9 H H H H H H H H Ph Ph D-10 H H H H H H H HPh Ph D-11 H H H H H H H H Ph Ph D-12 H H H H H H H H Ph Ph D-13 H H H HH H H H Ph Ph D-14 Ph H H H H H H Ph Ph Ph D-15

H H H H H H

Ph Ph D-16 CH3 H H H H H H CH3 Ph Ph D-17 H H H H X5 and X6 form a fusedring. H H H H D-18 H H H H X5 and X6 form a fused ring. H H Ph Ph D-19 HH H H X5 and X6 form a fused ring. H H

D-20 H H H H X5 and X6 form a fused ring. H H

D-21 H H H H X5 and X6 form a fused ring. H H CH3 CH3 D-22 H H H H X5and X6 form a fused ring. H H

D-23 H H H H X5 and X6 form a fused ring. H H

D-24 H H H H X5 and X6 form a fused ring. H H Ph Ph D-25 H H H H X5 andX6 form a fused ring. H H Ph Ph D-26 H H H H X5 and X6 form a fusedring. H H Ph Ph D-27 H H H H X5 and X6 form a fused ring. H H Ph Ph D-28H H H H X5 and X6 form a fused ring. H H Ph Ph D-29 H H H H X5 and X6form a fused ring. H H Ph Ph D-30 Ph H H H X5 and X6 form a fused ring.H Ph Ph Ph D-31

H H H X5 and X6 form a fused ring. H

Ph Ph D-32 CH3 H H H X5 and X6 form a fused ring. H CH3 Ph Ph CompoundNo. X15 X16 X17 X18 D-1 H H H H D-2 H H H H D-3 H H H H D-4 H H H H D-5H H H H D-6 H H H H D-7 H H H H D-8 Ph H H Ph D-9

H H

D-10 CH3 H H CH3 D-11 H Ph Ph H D-12 H

H D-13 H CH3 CH3 H D-14 H H H H D-15 H H H H D-16 H H H H D-17 H H H HD-18 H H H H D-19 H H H H D-20 H H H H D-21 H H H H D-22 H H H H D-23 HH H H D-24 Ph H H Ph D-25

H H

D-26 CH3 H H CH3 D-27 H Ph Ph H D-28 H

H D-29 H CH3 CH3 H D-30 H H H H D-31 H H H H D-32 H H H H

“A and B form a fused ring” in

means

Compound No. X1 X2 X3 X4 X5 X6 X7 X8 X11 D-33 H H H H H H H H H D-34 H HH H H H H H Ph D-35 H H H H H H H H

D-36 H H H H H H H H

D-37 H H H H H H H H CH3 D-38 H H H H H H H H

D-39 H H H H H H H H

D-40 H H H H H H H H Ph D-41 H H H H H H H H Ph D-42 H H H H H H H H PhD-43 Ph H H H H H H Ph Ph D-44

H H H H H H

Ph D-45 CH3 H H H H H H CH3 Ph D-46 H H H H X5 and X6 form a fused ring.H H H D-47 H H H H X5 and X6 form a fused ring. H H Ph D-48 H H H H X5and X6 form a fused ring. H H

D-49 H H H H X5 and X6 form a fused ring. H H

D-50 H H H H X5 and X6 form a fused ring. H H CH3 D-51 H H H H X5 and X6form a fused ring. H H

D-52 H H H H X5 and X6 form a fused ring. H H

D-53 H H H H X5 and X6 form a fused ring. H H Ph D-54 H H H H X5 and X6form a fused ring. H H Ph D-55 H H H H X5 and X6 form a fused ring. H HPh D-56 Ph H H H X5 and X6 form a fused ring. H Ph Ph D-57

H H H X5 and X6 form a fused ring. H

Ph D-58 CH3 H H H X5 and X6 form a fused ring. H CH3 Ph D-59 H X2 and X3form a fused ring. H H H H H H D-60 H X2 and X3 form a fused ring. H H HH H Ph D-61 H X2 and X3 form a fused ring. H H H H H

D-62 H X2 and X3 form a fused ring. H H H H H

D-63 H X2 and X3 form a fused ring. H H H H H CH3 D-64 H X2 and X3 forma fused ring. H H H H H

D-65 H X2 and X3 form a fused ring. H H H H H

D-66 H X2 and X3 form a fused ring. H H H H H Ph D-67 H X2 and X3 form afused ring. H H H H H Ph D-68 H X2 and X3 form a fused ring. H H H H HPh D-69 Ph X2 and X3 form a fused ring. H H H H Ph Ph D-70

X2 and X3 form a fused ring. H H H H

Ph D-71 CH3 X2 and X3 form a fused ring. H H H H CH3 Ph Compound No. X14X15 X16 D-33 H H H D-34 Ph H H D-35

H H D-36

H H D-37 CH3 H H D-38

H H D-39

H H D-40 Ph Ph Ph D-41 Ph

D-42 Ph CH3 CH3 D-43 Ph H H D-44 Ph H H D-45 Ph H H D-46 H H H D-47 Ph HH D-48

H H D-49

H H D-50 CH3 H H D-51

H H D-52

H H D-53 Ph Ph Ph D-54 Ph

D-55 Ph CH3 CH3 D-56 Ph H H D-57 Ph H H D-58 Ph H H D-59 H H H D-60 Ph HH D-61

H H D-62

H H D-63 CH3 H H D-64

H H D-65

H H D-66 Ph Ph Ph D-67 Ph

D-68 Ph CH3 CH3 D-69 Ph H H D-70 Ph H H D-71 Ph H H

“A and B form a fused ring” in

means

Compound No. X1 X2 X3 X4 X5 X6 X7 X8 X11 X14 D-72 H X2 and X3 form afused ring. H H H H H H H D-73 H X2 and X3 form a fused ring. H H H H HPh Ph D-74 H X2 and X3 form a fused ring. H H H H H

D-75 H X2 and X3 form a fused ring. H H H H H

D-76 H X2 and X3 form a fused ring. H H H H H CH3 CH3 D-77 H X2 and X3form a fused ring. H H H H H

D-78 H X2 and X3 form a fused ring. H H H H H

D-79 H X2 and X3 form a fused ring. H H H H H Ph Ph D-80 H X2 and X3form a fused ring. H H H H H Ph Ph D-81 H X2 and X3 form a fused ring. HH H H H Ph Ph D-82 H X2 and X3 form a fused ring. H H H H H Ph Ph D-83 HX2 and X3 form a fused ring. H H H H H Ph Ph D-84 H X2 and X3 form afused ring. H H H H H Ph Ph D-85 Ph X2 and X3 form a fused ring. H H H HPh Ph Ph D-86

X2 and X3 form a fused ring. H H H H

Ph Ph D-87 CH3 X2 and X3 form a fused ring. H H H H CH3 Ph Ph D-88 H X2and X3 form a fused ring. H H H H H H H D-89 H X2 and X3 form a fusedring. H H H H H Ph Ph D-90 H X2 and X3 form a fused ring. H H H H H

D-91 H X2 and X3 form a fused ring. H H H H H

D-92 H X2 and X3 form a fused ring. H H H H H CH3 CH3 D-93 H X2 and X3form a fused ring. H H H H H

D-94 H X2 and X3 form a fused ring. H H H H H

D-95 Ph X2 and X3 form a fused ring. H H H H Ph Ph Ph D-96

X2 and X3 form a fused ring. H H H H

Ph Ph D-97 CH3 X2 and X3 form a fused ring. H H H H CH3 Ph Ph CompoundNo. X15 X16 X17 X18 D-72 H H H H D-73 H H H H D-74 H H H H D-75 H H H HD-76 H H H H D-77 H H H H D-78 H H H H D-79 Ph H H Ph D-80

H H

D-81 CH3 H H CH3 D-82 H Ph Ph H D-83 H

H D-84 H CH3 CH3 H D-85 H H H H D-86 H H H H D-87 H H H H D-88 X15 andX16 form a fused ring. X17 and X18 form a fused ring. D-89 X15 and X16form a fused ring. X17 and X18 form a fused ring. D-90 X15 and X16 forma fused ring. X17 and X18 form a fused ring. D-91 X15 and X16 form afused ring. X17 and X18 form a fused ring. D-92 X15 and X16 form a fusedring. X17 and X18 form a fused ring. D-93 X15 and X16 form a fused ring.X17 and X18 form a fused ring. D-94 X15 and X16 form a fused ring. X17and X18 form a fused ring. D-95 X15 and X16 form a fused ring. X17 andX18 form a fused ring. D-96 X15 and X16 form a fused ring. X17 and X18form a fused ring. D-97 X15 and X16 form a fused ring. X17 and X18 forma fused ring.

[0285]

“A and B form a fused ring” in

means

Com- pound No. X2 X3 X6 X7 X11 = 21 X12 = X22 X13 = X23 X14 = X24 E-1 HH H H H H H H E-2 H H H H Ph H H Ph E-3 H H H H

H H

E-4 H H H H

H H

E-5 H H H H

H H

E-6 H H H H CH3 H H CH3 E-7 H H H H

H H

E-8 H H H H Ph Ph Ph Ph E-9 H H H H Ph

Ph E-10 H H H H Ph CH3 CH3 Ph E-11 Ph H Ph H Ph H H Ph E-12

H

H Ph H H Ph E-13 CH3 H CH3 H Ph H H Ph Compound No. X2 X3 X6 X7 X11 = 21X12 = X22 X13 X14 X23 X24 E-14 H H H H H H X13 and X14, X23 and X24 formfused rings. E-15 H H H H Ph H X13 and X14, X23 and X24 form fusedrings. E-16 H H H H

H X13 and X14, X23 and X24 form fused rings. E-17 H H H H

H X13 and X14, X23 and X24 form fused rings. E-18 H H H H

H X13 and X14, X23 and X24 form fused rings. E-19 H H H H CH3 H X13 andX14, X23 and X24 form fused rings. E-20 H H H H

H X13 and X14, X23 and X24 form fused rings. E-21 H H H H Ph Ph X13 andX14, X23 and X24 form fused rings. E-22 H H H H Ph

X13 and X14, X23 and X24 form fused rings. E-23 H H H H Ph CH3 X13 andX14, X23 and X24 form fused rings. E-24 Ph H H Ph Ph H X13 and X14, X23and X24 form fused rings. E-25

H H

Ph H X13 and X14, X23 and X24 form fused rings. E-26 CH3 H H CH3 Ph HX13 and X14, X23 and X24 form fused rings. Compound No. X2 X3 X6 X7 X11= X21 X12 = X22 X13 = X23 X14 = X24 E-27 H H H H X11 and X12, X21 andX22 form fused rings. X13 and X14, X23 and X24 form fused rings. E-28 PhH Ph H X11 and X12, X21 and X22 form fused rings. X13 and X14, X23 andX24 form fused rings. E-29

H

H X11 and X12, X21 and X22 form fused rings. X13 and X14, X23 and X24form fused rings. E-30 CH3 H CH3 H X11 and X12, X21 and X22 form fusedrings. X13 and X14, X23 and X24 form fused rings. Compound No. X2 X3 X6X7 X11 = 21 X12 = X22 E-31 H H H H H H E-32 H H H H Ph H E-33 H H H H

H E-34 H H H H

H E-35 H H H H

H E-36 H H H H CH3 H E-37 H H H H

H E-38 H H H H Ph Ph E-39 H H H H Ph

E-40 H H H H Ph CH3 E-41 Ph H Ph H Ph H E-42

H

H Ph H E-43 CH3 H CH3 H Ph H Compound No. X13 X14 X23 X24 E-31 X13 andX14 form a fused ring. H H E-32 X13 and X14 form a fused ring. H Ph E-33X13 and X14 form a fused ring. H

E-34 X13 and X14 form a fused ring. H

E-35 X13 and X14 form a fused ring. H

E-36 X13 and X14 form a fused ring. H CH3 E-37 X13 and X14 form a fusedring. H

E-38 X13 and X14 form a fused ring. Ph Ph E-39 X13 and X14 form a fusedring.

Ph E-40 X13 and X14 form a fused ring. CH3 Ph E-41 X13 and X14 form afused ring. H Ph E-42 X13 and X14 form a fused ring. H Ph E-43 X13 andX14 form a fused ring. H Ph Compound No. X2 X3 X6 X7 X11       X12 X13      X14 E-44 H H H H X11 and X12 form a fused ring. X13 and X14 form afused ring. E-45 H H H H X11 and X12 form a fused ring. X13 and X14 forma fused ring. E-46 H H H H X11 and X12 form a fused ring. X13 and X14form a fused ring. E-47 H H H H X11 and X12 form a fused ring. X13 andX14 form a fused ring. E-48 H H H H X11 and X12 form a fused ring. X13and X14 form a fused ring. E-49 H H H H X11 and X12 form a fused ring.X13 and X14 form a fused ring. E-50 H H H H X11 and X12 form a fusedring. X13 and X14 form a fused ring. E-51 H H H H X11 and X12 form afused ring. X13 and X14 form a fused ring. E-52 H H H H X11 and X12 forma fused ring. X13 and X14 form a fused ring. E-53 H H H H X11 and X12form a fused ring. X13 and X14 form a fused ring. E-54 Ph H Ph H X11 andX12 form a fused ring. X13 and X14 form a fused ring. E-55

H

H X11 and X12 form a fused ring. X13 and X14 form a fused ring. E-56 CH3H CH3 H X11 and X12 form a fused ring. X13 and X14 form a fused ring.Compound No. X21 X22 X23 X24 E-44 H H H H E-45 Ph H H Ph E-46

H H

E-47

H H

E-48

H H

E-49 CH3 H H CH3 E-50

H H

E-51 Ph Ph Ph Ph E-52 Ph

Ph E-53 Ph CH3 CH3 Ph E-54 Ph H H Ph E-55 Ph H H Ph E-56 Ph H H PhCompound No. X2 X3 X6 X7 X11 = 21 X12 E-57 H H H H H H E-58 H H H H Ph HE-59 H H H H

H E-60 H H H H

H E-61 H H H H

H E-62 H H H H CH3 H E-63 H H H H

H E-64 H H H H Ph Ph E-65 H H H H Ph

E-66 H H H H Ph CH3 E-67 Ph H Ph H Ph H E-68

H

H Ph H E-69 CH3 H CH3 H Ph H Compound No. X13 X14 X22 X23 X24 E-57 X13and X14 form a fused ring. X22 and X23 form a fused ring. H E-58 X13 andX14 form a fused ring. X22 and X23 form a fused ring. Ph E-59 X13 andX14 form a fused ring. X22 and X23 form a fused ring.

E-60 X13 and X14 form a fused ring. X22 and X23 form a fused ring.

E-61 X13 and X14 form a fused ring. X22 and X23 form a fused ring.

E-62 X13 and X14 form a fused ring. X22 and X23 form a fused ring. CH3E-63 X13 and X14 form a fused ring. X22 and X23 form a fused ring.

E-64 X13 and X14 form a fused ring. X22 and X23 form a fused ring. PhE-65 X13 and X14 form a fused ring. X22 and X23 form a fused ring. PhE-66 X13 and X14 form a fused ring. X22 and X23 form a fused ring. PhE-67 X13 and X14 form a fused ring. X22 and X23 form a fused ring. PhE-68 X13 and X14 form a fused ring. X22 and X23 form a fused ring. PhE-69 X13 and X14 form a fused ring. X22 and X23 form a fused ring. PhCompound No. X2 X3 X6 X7 X11 = 24 X12 = X23 E-70 H H H H H H E-71 H H HH Ph H E-72 H H H H

H E-73 H H H H

H E-74 H H H H

H E-75 H H H H CH3 H E-76 H H H H

H E-77 H H H H Ph Ph E-78 H H H H Ph

E-79 H H H H Ph CH3 E-80 Ph H Ph H Ph H E-81

H

H Ph H E-82 CH3 H CH3 H Ph H Compound No. X13 X14 X21 X22 E-70 X13 andX14 form a fused ring. X21 and X22 form a fused ring. E-71 X13 and X14form a fused ring. X21 and X22 form a fused ring. E-72 X13 and X14 forma fused ring. X21 and X22 form a fused ring. E-73 X13 and X14 form afused ring. X21 and X22 form a fused ring. E-74 X13 and X14 form a fusedring. X21 and X22 form a fused ring. E-75 X13 and X14 form a fused ring.X21 and X22 form a fused ring. E-76 X13 and X14 form a fused ring. X21and X22 form a fused ring. E-77 X13 and X14 form a fused ring. X21 andX22 form a fused ring. E-78 X13 and X14 form a fused ring. X21 and X22form a fused ring. E-79 X13 and X14 form a fused ring. X21 and X22 forma fused ring. E-80 X13 and X14 form a fused ring. X21 and X22 form afused ring. E-81 X13 and X14 form a fused ring. X21 and X22 form a fusedring. E-82 X13 and X14 form a fused ring. X21 and X22 form a fused ring.Compound No. X2 X3 X6 X7  X11 X12  X13 X14 E-83 H H H H X11 and X12 forma fused ring. X13 and X14 form a fused ring. E-84 H H H H X11 and X12form a fused ring. X13 and X14 form a fused ring. E-85 H H H H X11 andX12 form a fuaed ring. X13 and X14 form a fused ring. E-86 H H H H X11and X12 form a fuaed ring. X13 and X14 form a fused ring. E-87 H H H HX11 and X12 form a fused ring. X13 and X14 form a fused ring. E-88 H H HH X11 and X12 form a fused ring. X13 and X14 form a fused ring. E-89 H HH H X11 and X12 form a fused ring. X13 and X14 form a fused ring. E-90Ph H Ph H X11 and X12 form a fused ring. X13 and X14 form a fused ring.E-91

H

H X11 and X12 form a fused ring. X13 and X14 form a fused ring. E-92 CH3H CH3 H X11 and X12 form a fused ring. X13 and X14 form a fused ring.Compound No. X21 X22 X23 X24 E-83 H X22 and X23 form a fused ring. HE-84 Ph X22 and X23 form a fused ring. Ph E-85

X22 and X23 form a fused ring.

E-86

X22 and X23 form a fused ring.

E-87

X22 and X23 form a fused ring.

E-88 CH3 X22 and X23 form a fused ring. CH3 E-89

X22 and X23 form a fused ring.

E-90 Ph X22 and X23 form a fused ring. Ph E-91 Ph X22 and X23 form afused ring. Ph E-92 Ph X22 and X23 form a fused ring. Ph Compound No. X2 X3 X6 X7 X11 X12 X13 X14 E-93 X2 and X3 form a fused ring. H H H HX13 and X14 form a fused ring. E-94 X2 and X3 form a fused ring. H H PhH X13 and X14 form a fused ring. E-95 X2 and X3 form a fused ring. H H

H X13 and X14 form a fused ring. E-96 X2 and X3 form a fused ring. H H

H X13 and X14 form a fused ring. E-97 X2 and X3 form a fused ring. H H

H X13 and X14 form a fused ring. E-98 X2 and X3 form a fused ring. H HCH3 H X13 and X14 form a fused ring. E-99 X2 and X3 form a fused ring. HH

H X13 and X14 form a fused ring. E-100 X2 and X3 form a fused ring. H HPh Ph X13 and X14 form a fused ring. E-101 X2 and X3 form a fused ring.H H Ph

X13 and X14 form a fused ring. E-102 X2 and X3 form a fused ring. H H PhCH3 X13 and X14 form a fused ring. E-103 X2 and X3 form a fused ring. PhH Ph H X13 and X14 form a fused ring. E-104 X2 and X3 form a fused ring.

H Ph H X13 and X14 form a fused ring. E-105 X2 and X3 form a fused ring.CH3 H Ph H X13 and X14 form a fused ring. Compound No. X21 X22 X23 X24E-93 X21 and X22 form a fused ring. H H E-94 X21 and X22 form a fusedring. H Ph E-95 X21 and X22 form a fused ring. H

E-96 X21 and X22 form a fused ring. H

E-97 X21 and X22 form a fused ring. H

E-98 X21 and X22 form a fused ring. H CH3 E-99 X21 and X22 form a fusedring. H

E-100 X21 and X22 form a fused ring. Ph Ph E-101 X21 and X22 form afused ring.

Ph E-102 X21 and X22 form a fused ring. CH3 Ph E-103 X21 and X22 form afused ring. H Ph E-104 X21 and X22 form a fused ring. H Ph E-105 X21 andX22 form a fused ring. H Ph Com- pound No. X2 X3 X6 X7 X11 = 21 X12 =X22 X13 = X23 X14 = X24 E-106 X2 and X3 form a fused ring. H H H H H HE-107 X2 and X3 form a fused ring. H H Ph H H Ph E-108 X2 and X3 form afused ring. H H

H H

E-109 X2 and X3 form a fused ring. H H

H H

E-110 X2 and X3 form a fused ring. H H

H H

E-111 X2 and X3 form a fused ring. H H CH3 H H CH3 E-112 X2 and X3 forma fused ring. H H

H H

E-113 X2 and X3 form a fused ring. H H Ph Ph Ph Ph E-114 X2 and X3 forma fused ring. H H Ph

Ph E-115 X2 and X3 form a fused ring. H H Ph CH3 CH3 Ph E-116 X2 and X3form a fused ring. Ph H Ph H H Ph E-117 X2 and X3 form a fused ring.

H Ph H H Ph E-118 X2 and X3 form a fused ring. CH3 H Ph H H Ph CompoundNo. X2      X3 X6 X7 X11 = 21 X12 E-119 X2 and X3 form a fused ring. H HH H E-120 X2 and X3 form a fused ring. H H Ph H E-121 X2 and X3 form afused ring. H H

H E-122 X2 and X3 form a fused ring. H H

H E-123 X2 and X3 form a fused ring. H H

H E-124 X2 and X3 form a fused ring. H H CH3 H E-125 X2 and X3 form afused ring. H H

H E-126 X2 and X3 form a fused ring. H H Ph Ph E-127 X2 and X3 form afused ring. H H Ph

E-128 X2 and X3 form a fused ring. H H Ph CH3 E-129 X2 and X3 form afused ring. Ph H Ph H E-130 X2 and X3 form a fused ring.

H Ph H E-131 X2 and X3 form a fused ring. CH3 H Ph H Compound No. X13X22 X23 X14 = X24 E-119 H X22 and X23 form a fused ring. H E-120 H X22and X23 form a fused ring. Ph E-121 H X22 and X23 form a fused ring.

E-122 H X22 and X23 form a fused ring.

E-123 H X22 and X23 form a fused ring.

E-124 H X22 and X23 form a fused ring. CH3 E-125 H X22 and X23 form afused ring.

E-126 Ph X22 and X23 form a fused ring. Ph E-127

X22 and X23 form a fused ring. Ph E-128 CH3 X22 and X23 form a fusedring. Ph E-129 H X22 and X23 form a fused ring. Ph E-130 H X22 and X23form a fused ring. Ph E-131 H X22 and X23 form a fused ring. Ph CompoundNo. X2 X3 X6 X7 X11 = 21 X12 = X22 X13 = X23 X14 = X24 E-132 X2 and X3form a fused ring. X6 and X7 form a fused ring. H H H H E-133 X2 and X3form a fused ring. X6 and X7 form a fused ring. Ph H H Ph E-134 X2 andX3 form a fused ring. X6 and X7 form a fused ring.

H H

E-135 X2 and X3 form a fused ring. X6 and X7 form a fused ring.

H H

E-136 X2 and X3 form a fused ring. X6 and X7 form a fused ring.

H H

E-137 X2 and X3 form a fused ring. X6 and X7 form a fused ring. CH3 H HCH3 E-138 X2 and X3 form a fused ring. X6 and X7 form a fused ring.

H H

E-139 X2 and X3 form a fused ring. X6 and X7 form a fused ring. Ph Ph PhPh E-140 X2 and X3 form a fused ring. X6 and X7 form a fused ring. Ph

Ph E-141 X2 and X3 form a fused ring. X6 and X7 form a fused ring. PhCH3 CH3 Ph Compound No. X2       X3 X6       X7 X11 = 21 X12 E-142 X2and X3 form a fused ring. X6 and X7 form a fused ring. H H E-143 X2 andX3 form a fused ring. X6 and X7 form a fused ring. Ph H E-144 X2 and X3form a fused ring. X6 and X7 form a fused ring.

H E-145 X2 and X3 form a fused ring. X6 and X7 form a fused ring.

H E-146 X2 and X3 form a fused ring. X6 and X7 form a fused ring.

H E-147 X2 and X3 form a fused ring. X6 and X7 form a fused ring. CH3 HE-148 X2 and X3 form a fused ring. X6 and X7 form a fused ring.

H E-149 X2 and X3 form a fused ring. X6 and X7 form a fused ring. Ph PhE-150 X2 and X3 form a fused ring. X6 and X7 form a fused ring. Ph

E-151 X2 and X3 form a fused ring. X6 and X7 form a fused ring. Ph CH3Compound No. X13 X22 X23 X14 = X24 E-142 H X22 and X23 form a fusedring. H E-143 H X22 and X23 form a fused ring. Ph E-144 H X22 and X23form a fused ring.

E-145 H X22 and X23 form a fused ring.

E-146 H X22 and X23 form a fused ring.

E-147 H X22 and X23 form a fused ring. CH3 E-148 H X22 and X23 form afused ring.

E-149 Ph X22 and X23 form a fused ring. Ph E-150

X22 and X23 form a fused ring. Ph E-151 CH3 X22 and X23 form a fusedring. Ph Compound No. X2       X3 X6       X7 X11 = 21 X12 = 22 E-152 X2and X3 form a fused ring. X6 and X7 form a fused ring. H H E-153 X2 andX3 form a fused ring. X6 and X7 form a fused ring. Ph H E-154 X2 and X3form a fused ring. X6 and X7 form a fused ring.

H E-155 X2 and X3 form a fused ring. X6 and X7 form a fused ring.

H E-156 X2 and X3 form a fused ring. X6 and X7 form a fused ring.

H E-157 X2 and X3 form a fused ring. X6 and X7 form a fused ring. CH3 HE-158 X2 and X3 form a fused ring. X6 and X7 form a fused ring.

H E-159 X2 and X3 form a fused ring. X6 and X7 form a fused ring. Ph PhE-160 X2 and X3 form a fused ring. X6 and X7 form a fused ring. Ph

E-161 X2 and X3 forms fused ring. X6 and X7 form a fused ring. Ph CH3Compound No. X13 X14 X23 X24 E-152 X13 and X14 form a fused ring. H HE-153 X13 and X14 form a fused ring. H Ph E-154 X13 and X14 form a fusedring. H

E-155 X13 and X14 form a fused ring. H

E-156 X13 and X14 form a fused ring. H

E-157 X13 and X14 form a fused ring. H CH3 E-158 X13 and X14 form afused ring. H

E-159 X13 and X14 form a fused ring. Ph Ph E-160 X13 and X14 form afused ring.

Ph E-161 X13 and X14 form a fused ring. CH3 Ph Compound No. X2 X3 X6 X7X11 = 21 X12 = X22 X13 X14 X23 X24 E-162 X2 and X3 form a fused ring. X6and X7 form a fused ring. H H X13 and X14 form a fused ring. X23 and X24form a fused ring. E-163 X2 and X3 form a fused ring. X6 and X7 form afused ring. Ph H X13 and X14 form a fused ring. X23 and X24 form a fusedring. E-164 X2 and X3 form a fused ring. X6 and X7 form a fused ring.

H X13 and X14 form a fused ring. X23 and X24 form a fused ring. E-165 X2and X3 form a fused ring. X6 and X7 form a fused ring.

H X13 and X14 form a fused ring. X23 and X24 form a fused ring. E-166 X2and X3 form a fused ring. X6 and X7 form a fused ring.

H X13 and X14 form a fused ring. X23 and X24 form a fused ring. E-167 X2and X3 form a fused ring. X6 and X7 form a fused ring. CH3 H X13 and X14form a fused ring. X23 and X24 form a fused ring. E-168 X2 and X3 form afused ring. X6 and X7 form a fused ring.

H X13 and X14 form a fused ring. X23 and X24 form a fused ring. E-169 X2and X3 form a fused ring. X6 and X7 form a fused ring. Ph Ph X13 and X14form a fused ring. X23 and X24 form a fused ring. E-170 X2 and X3 form afused ring. X6 and X7 form a fused ring. Ph

X13 and X14 form a fused ring. X23 and X24 form a fused ring. E-171 X2and X3 form a fused ring. X6 and X7 form a fused ring. Ph CH3 X13 andX14 form a fused ring. X23 and X24 form a fused ring. Compound No. X2      X3 X6       X7 X11 X12 X13 X14 E-172 X2 and X3 form a fused ring.X6 and X7 form a fused ring. H H X13 and X14 form a fused ring. E-173 X2and X3 form a fused ring. X6 and X7 form a fused ring. Ph H X13 and X14form a fused ring. E-174 X2 and X3 form a fused ring. X6 and X7 form afused ring.

H X13 and X14 form a fused ring. E-175 X2 and X3 form a fused ring. X6and X7 form a fused ring.

H X13 and X14 form a fused ring. E-176 X2 and X3 form a fused ring. X6and X7 form a fused ring.

H X13 and X14 form a fused ring. E-177 X2 and X3 form a fused ring. X6and X7 form a fused ring. CH3 H X13 and X14 form a fused ring. E-178 X2and X3 form a fused ring. X6 and X7 form a fused ring.

H X13 and X14 form a fused ring. E-179 X2 and X3 form a fused ring. X6and X7 form a fused ring. Ph Ph X13 and X14 form a fused ring. E-180 X2and X3 form a fused ring. X6 and X7 form a fused ring. Ph

X13 and X14 form a fused ring. E-181 X2 and X3 form a fused ring. X6 andX7 form a fused ring. Ph CH3 X13 and X14 form a fused ring. Compound No.X21 X22 X23 X24 E-172 X21 and X22 form a fused ring. H H E-173 X21 andX22 form a fused ring. H Ph E-174 X21 and X22 form a fused ring. H

E-175 X21 and X22 form a fused ring. H

E-176 X21 and X22 form a fused ring. H

E-177 X21 and X22 form a fused ring. H CH3 E-178 X21 and X22 form afused ring. H

E-179 X21 and X22 form a fused ring. Ph Ph E-180 X21 and X22 form afused ring.

Ph E-181 X21 and X22 form a fused ring. CH3 Ph Compound No. X2       X3X6       X7 X11 = 21 X12 E-182 X2 and X3 form a fused ring. X6 and X7form a fused ring. H H E-183 X2 and X3 form a fused ring. X6 and X7 forma fused ring. Ph H E-184 X2 and X3 form a fused ring. X6 and X7 form afused ring.

H E-185 X2 and X3 form a fused ring. X6 and X7 form a fused ring.

H E-186 X2 and X3 form a fused ring. X6 and X7 form a fused ring.

H E-187 X2 and X3 form a fused ring. X6 and X7 form a fused ring. CH3 HE-188 X2 and X3 form a fused ring. X6 and X7 form a fused ring.

H E-189 X2 and X3 form a fused ring. X6 and X7 form a fused ring. Ph PhE-190 X2 and X3 form a fused ring. X6 and X7 form a fused ring. Ph

E-191 X2 and X3 form a fused ring. X6 and X7 form a fused ring. Ph CH3Compound No. X13 X14 X22 X23 X24 E-182 X13 and X14 form a fused ring.X22 and X23 form a fused ring. H E-183 X13 and X14 form a fused ring.X22 and X23 form a fused ring. Ph E-184 X13 and X14 form a fused ring.X22 and X23 form a fused ring.

E-185 X13 and X14 form a fused ring. X22 and X23 form a fused ring.

E-186 X13 and X14 form a fused ring. X22 and X23 form a fused ring.

E-187 X13 and X14 form a fused ring. X22 and X23 form a fused ring. CH3E-188 X13 and X14 form a fused ring. X22 and X23 form a fused ring.

E-189 X13 and X14 form a fused ring. X22 and X23 form a fused ring. PhE-190 X13 and X14 form a fused ring. X22 and X23 form a fused ring. PhE-191 X13 and X14 form a fused ring. X22 and X23 form a fused ring. Ph

[0286]

“A and B form a fused ring” in

means

Compound No. X2 X3 X6 X7 X11 = X21 X14 = X24 X15 = X25 F-1 H H H H H H HF-2 H H H H Ph Ph H F-3 H H H H

H F-4 H H H H

H F-5 H H H H

H F-6 H H H H CH3 CH3 H F-7 H H H H

H F-8 H H H H Ph Ph Ph F-9 H H H H Ph Ph

F-10 H H H H Ph Ph CH3 F-11 H H H H Ph Ph H F-12 H H H H Ph Ph H F-13 HH H H Ph Ph H F-14 X2 and X3 form a fused ring. H H H H H F-15 X2 and X3form a fused ring. H H Ph Ph H F-16 X2 and X3 form a fused ring. H H

H F-17 X2 and X3 form a fused ring. H H

H F-18 X2 and X3 form a fused ring. H H

H F-19 X2 and X3 form a fused ring. H H CH3 CH3 H F-20 X2 and X3 form afused ring. H H

H F-21 X2 and X3 form a fused ring. H H Ph Ph Ph F-22 X2 and X3 form afused ring. H H Ph Ph

F-23 X2 and X3 form a fused ring. H H Ph Ph CH3 F-24 X2 and X3 form afused ring. H H Ph Ph H F-25 X2 and X3 form a fused ring. H H Ph Ph HF-26 X2 and X4 form a fused ring. H H Ph Ph H Compound No. X16 = X26 X17= X27 X18 = X28 F-1 H H H F-2 H H H F-3 H H H F-4 H H H F-5 H H H F-6 HH H F-7 H H H F-8 H H Ph F-9 H H

F-10 H H CH3 F-11 Ph Ph H F-12

H F-13 CH3 CH3 H F-14 H H H F-15 H H H F-16 H H H F-17 H H H F-18 H H HF-19 H H H F-20 H H H F-21 H H Ph F-22 H H

F-23 H H CH3 F-24 Ph Ph H F-25

H F-26 CH3 CH3 H Compound No. X2 X3 X6 X7 X11 = X21 X14 = X24 X15 = X25X16       X17 F-27 H H H H H H H X16 and X17 form a fused ring. F-28 H HH H Ph Ph H X16 and X17 form a fused ring. F-29 H H H H

H X16 and X17 form a fused ring. F-30 H H H H

H X16 and X17 form a fused ring. F-31 H H H H

H X16 and X17 form a fused ring. F-32 H H H H CH3 CH3 H X16 and X17 forma fused ring. F-33 H H H H

H X16 and X17 form a fused ring. F-34 H H H H Ph Ph Ph X16 and X17 forma fused ring. F-35 H H H H Ph Ph

X16 and X17 form a fused ring. F-36 H H H H Ph Ph CH3 X16 and X17 form afused ring. F-37 H H H H Ph Ph H X16 and X17 form a fused ring. F-38 H HH H Ph Ph H X16 and X17 form a fused ring. F-39 H H H H Ph Ph H X16 andX17 form a fused ring. Compound No. X18 = X28 X26 X27 F-27 H H H F-28 HH H F-29 H H H F-30 H H H F-31 H H H F-32 H H H F-33 H H H F-34 Ph H HF-35

H H F-36 CH3 H H F-37 H H Ph F-38 H H

F-39 H H CH3 Compound No. X2 X3 X6 X7 X11 = X21 X14 = X24 X15 = X25 X16      X17 F-40 H H H H H H H X16 and X17 form a fused ring. F-41 H H H HPh Ph H X16 and X17 form a fused ring. F-42 H H H H

H X16 and X17 form a fused ring. F-43 H H H H

H X16 and X17 form a fused ring. F-44 H H H H

H X16 and X17 form a fused ring. F-45 H H H H CH3 CH3 H X16 and X17 forma fused ring. F-46 H H H H

H X16 and X17 form a fused ring. F-47 H H H H Ph Ph Ph X16 and X17 forma fused ring. F-48 H H H H Ph Ph

X16 and X17 form a fused ring. F-49 H H H H Ph Ph CH3 X16 and X17 form afused ring. Compound No. X18 = X28 X26       X27 F-40 H X26 and X27 forma fused ring. F-41 H X26 and X27 form a fused ring. F-42 H X26 and X27form a fused ring. F-43 H X26 and X27 form a fused ring. F-44 H X26 andX27 form a fused ring. F-45 H X26 and X27 form a fused ring. F-46 H X26and X27 form a fused ring. F-47 Ph X26 and X27 form a fused ring. F-48

X26 and X27 form a fused ring. F-49 CH3 X26 and X27 form a fused ring.Compound No. X2       X3 X6       X7 X11 = X21 X14 = X24 X15 = X25 F-50X2 and X3 form a fused ring. X6 and X7 form a fused ring. H H H F-51 X2and X3 form a fused ring. X6 and X7 form a fused ring. Ph Ph H F-52 X2and X3 form a fused ring. X6 and X7 form a fused ring.

H F-53 X2 and X3 form a fused ring. X6 and X7 form a fused ring.

H F-54 X2 and X3 form a fused ring. X6 and X7 form a fused ring.

H F-55 X2 and X3 form a fused ring. X6 and X7 form a fused ring. CH3 CH3H F-56 X2 and X3 form a fused ring. X6 and X7 form a fused ring.

H F-57 X2 and X3 form a fused ring. X6 and X7 form a fused ring. Ph PhPh F-58 X2 and X3 form a fused ring. X6 and X7 form a fused ring. Ph Ph

F-59 X2 and X3 form a fused ring. X6 and X7 form a fused ring. Ph Ph CH3F-60 X2 and X3 form a fused ring. X6 and X7 form a fused ring. Ph Ph HF-61 X2 and X3 form a fused ring. X6 and X7 form a fused ring. Ph Ph HF-62 X2 and X3 form a fused ring. X6 and X7 form a fused ring. Ph Ph HCompound No. X16 = X26 X17 = X27 X18 = X28 F-50 H H H F-51 H H H F-52 HH H F-53 H H H F-54 H H H F-55 H H H F-56 H H H F-57 H H Ph F-58 H H

F-59 H H CH3 F-60 Ph Ph H F-61

H F-62 CH3 CH3 H Compound No. X2 X3 X6 X7 X11 = X21 X15 X16 X14 = X24X25 F-63 X2 and X3 form a fused ring. X6 and X7 form a fused ring. H X15and X16 form a fused ring. H H F-64 X2 and X3 form a fused ring. X6 andX7 form a fused ring. Ph X15 and X16 form a fused ring. Ph H F-65 X2 andX3 form a fused ring. X6 and X7 form a fused ring.

X15 and X16 form a fused ring.

H F-66 X2 and X3 form a fused ring. X6 and X7 form a fused ring.

X15 and X16 form a fused ring.

H F-67 X2 and X3 form a fused ring. X6 and X7 form a fused ring.

X15 and X16 form a fused ring.

H F-68 X2 and X3 form a fused ring. X6 and X7 form a fused ring. CH3 X15and X16 form a fused ring. CH3 H F-69 X2 and X3 form a fused ring. X6and X7 form a fused ring.

X15 and X16 form a fused ring.

H F-70 X2 and X3 form a fused ring. X6 and X7 form a fused ring. Ph X15and X16 form a fused ring. Ph Ph F-71 X2 and X3 form a fused ring. X6and X7 form a fused ring. Ph X15 and X16 form a fused ring. Ph

F-72 X2 and X3 form a fused ring. X6 and X7 form a fused ring. Ph X15and X16 form a fused ring. Ph CH3 F-73 X2 and X3 form a fused ring. X6and X7 form a fused ring. Ph X15 and X16 form a fused ring. Ph H F-74 X2and X3 form a fused ring. X6 and X7 form a fused ring. Ph X15 and X16form a fused ring. Ph H F-75 X2 and X3 form a fused ring. X6 and X7 forma fused ring. Ph X15 and X16 form a fused ring. Ph H Compound No. X26X17 = X27 X18 = X28 F-63 H H H F-64 H H H F-65 H H H F-66 H H H F-67 H HH F-68 H H H F-69 H H H F-70 H H Ph F-71 H H

F-72 H H CH3 F-73 Ph Ph H F-74

H F-75 CH3 CH3 H Compound No. X2 X3 X6 X7 X11 = X21 X15 X16 X17 X18 X14= X24 F-76 X2 and X3 form a fused ring. X6 and X7 form a fused ring. HX15 and X16 form a fused ring. X17 and X18 form a fused ring. H F-77 X2and X3 form a fused ring. X6 and X7 form a fused ring. Ph X15 and X16form a fused ring. X17 and X18 form a fused ring. Ph F-78 X2 and X3 forma fused ring. X6 and X7 form a fused ring

X15 and X16 form a fused ring. X17 and X18 form a fused ring.

F-79 X2 and X3 form a fused ring. X6 and X7 form a fused ring.

X15 and X16 form a fused ring. X17 and X18 form a fused ring.

F-80 X2 and X3 form a fused ring. X6 and X7 form a fused ring.

X15 and X16 form a fused ring. X17 and X18 form a fused ring.

F-81 X2 and X3 form a fused ring. X6 and X7 form a fused ring. CH3 X15and X16 form a fused ring. X17 and X18 form a fused ring. CH3 F-82 X2and X3 form a fused ring. X6 and X7 form a fused ring

X15 and X16 form a fused ring. X17 and X18 form a fused ring.

F-83 X2 and X3 form a fused ring. X6 and X7 form a fused ring. Ph X15and X16 form a fused ring. X17 and X18 form a fused ring. Ph F-84 X2 andX3 form a fused ring. X6 and X7 form a fused ring. Ph X15 and X16 form afused ring. X17 and X18 form a fused ring. Ph F-85 X2 and X3 form afused ring. X6 and X7 form a fused ring. Ph X15 and X16 form a fusedring. X17 and X18 form a fused ring. Ph F-86 X2 and X3 form a fusedring. X6 and X7 form a fused ring. Ph X15 and X16 form a fused ring. X17and X18 form a fused ring. Ph F-87 X2 and X3 form a fused ring. X6 andX7 form a fused ring. Ph X15 and X16 form a fused ring. X17 and X18 forma fused ring. Ph F-88 X2 and X3 form a fused ring. X6 and X7 form afused ring. Ph X15 and X16 form a fused ring. X17 and X18 form a fusedring. Ph Compound No. X25 X26 X27 X28 F-76 H H H H F-77 H H H H F-78 H HH H F-79 H H H H F-80 H H H H F-81 H H H H F-82 H H H H F-83 Ph H H PhF-84

H H

F-85 CH3 H H CH3 F-86 H Ph Ph H F-87 H

H F-88 H CH3 CH3 H Compound No. X2 X3 X6 X7 X11 = X21 X15 X16 X17 X18F-89 X2 and X3 form a fused ring. X6 and X7 form a fused ring. H X15 andX16 form a fused ring. H H F-90 X2 and X3 form a fused ring. X6 and X7form a fused ring. Ph X15 and X16 form a fused ring. H H F-91 X2 and X3form a fused ring. X6 and X7 form a fused ring.

X15 and X16 form a fused ring. H H F-92 X2 and X3 form a fused ring. X6and X7 form a fused ring.

X15 and X16 form a fused ring. H H F-93 X2 and X3 form a fused ring. X6and X7 form a fused ring.

X15 and X16 form a fused ring. H H F-94 X2 and X3 form a fused ring. X6and X7 form a fused ring. CH3 X15 and X16 form a fused ring. H H F-95 X2and X3 form a fused ring. X6 and X7 form a fused ring.

X15 and X16 form a fused ring. H H F-96 X2 and X3 form a fused ring. X6and X7 form a fused ring. Ph X15 and X16 form a fused ring. H H F-97 X2and X3 form a fused ring. X6 and X7 form a fused ring. Ph X15 and X16form a fused ring.

H F-98 X2 and X3 form a fused ring. X6 and X7 form a fused ring. Ph X15and X16 form a fused ring. CH3 H F-99 X2 and X3 form a fused ring. X6and X7 form a fused ring. Ph X15 and X16 form a fused ring. H Ph F-100X2 and X3 form a fused ring. X6 and X7 form a fused ring. Ph X15 and X16form a fused ring. H

F-101 X2 and X3 form a fused ring. X6 and X7 form a fused ring. Ph X15and X16 form a fused ring. H CH3 Compound No. X14 = X24 X25 X26 X27 X28F-89 H X25 and X26 form a fused ring. H H F-90 Ph X25 and X26 form afused ring. H H F-91

X25 and X26 form a fused ring. H H F-92

X25 and X26 form a fused ring. H H F-93

X25 and X26 form a fused ring. H H F-94 CH3 X25 and X26 form a fusedring. H H F-95

X25 and X26 form a fused ring. H H F-96 Ph X25 and X26 form a fusedring. H Ph F-97 Ph X25 and X26 form a fused ring. H

F-98 Ph X25 and X26 form a fused ring. H CH3 F-99 Ph X25 and X26 form afused ring. Ph H F-100 Ph X25 and X26 form a fused ring.

H F-101 Ph X25 and X26 form a fused ring. CH3 H Compound No. X2       X3X6       X7 X11 = X21 X14 = X24 X15 = X25 F-102 X2 and X3 form a fusedring. X6 and X7 form a fused ring. H H H F-103 X2 and X3 form a fusedring. X6 and X7 form a fused ring. Ph Ph H F-104 X2 and X3 form a fusedring. X6 and X7 form a fused ring.

H F-105 X2 and X3 form a fused ring. X6 and X7 form a fused ring.

H F-106 X2 and X3 form a fused ring. X6 and X7 form a fused ring.

H F-107 X2 and X3 form a fused ring. X6 and X7 form a fused ring. CH3CH3 H F-108 X2 and X3 form a fused ring. X6 and X7 form a fused ring.

H F-109 X2 and X3 form a fused ring. X6 and X7 form a fused ring. Ph PhPh F-110 X2 and X3 form a fused ring. X6 and X7 form a fused ring. Ph Ph

F-111 X2 and X3 form a fused ring. X6 and X7 form a fused ring. Ph PhCH3 Compound No. X16 = X26 X17 = X27 X18 = X28 F-102 X16 and X17, X26and X27 form fused rings. H F-103 X16 and X17, X26 and X27 form fusedrings. H F-104 X16 and X17, X26 and X27 form fused rings. H F-105 X16and X17, X26 and X27 form fused rings. H F-106 X16 and X17, X26 and X27form fused rings. H F-107 X16 and X17, X26 and X27 form fused rings. HF-108 X16 and X17, X26 and X27 form fused rings. H F-109 X16 and X17,X26 and X27 form fused rings. Ph F-110 X16 and X17, X26 and X27 formfused rings.

F-111 X16 and X17, X26 and X27 form fused rings. CH3

“A and B form a fused ring” in

means

Com- pound X- X- No. X2 X3 X6 X7 X32 X33 36 37 X11 X12 F-112 H H H H H HH H H H F-113 H H H H H H H H Ph H F-114 H H H H H H H H

H F-115 H H H H H H H H

H F-116 H H H H H H H H

H F-117 H H H H H H H H CH3 H F-118 H H H H H H H H

H F-119 Ph H H H Ph H H H Ph H F-120

H H H

H H H Ph H F-121 CH3 H H H CH3 H H H Ph H F-122 H Ph H H H Ph H H Ph HF-123 H

H H H

H H Ph H F-124 H CH3 H H H CH3 H H Ph H F-125 H H H H H H H H Ph PhF-126 H H H H H H H H Ph

F-127 H H H H H H H H Ph CH3 Com- pound No. X13 X14 X21 X22 X23 X24F-112 H H H H H H F-113 H Ph Ph H H Ph F-114 H

H H

F-115 H

H H

F-116 H

H H

F-117 H CH3 CH3 H H CH3 F-118 H

H H

F-119 H Ph Ph H H Ph F-120 H Ph Ph H H Ph F-121 H Ph Ph H H Ph F-122 HPh Ph H H Ph F-123 H Ph Ph H H Ph F-124 H Ph Ph H H Ph F-125 Ph Ph Ph PhPh Ph F-126

Ph Ph

Ph F-127 CH3 Ph Ph CH3 CH3 Ph Compound No. X2 X3 X6 X7 X32 X33 X36 X37X11 F-128 H H H H H H H H H F-129 H H H H H H H H Ph F-130 H H H H H H HH

F-131 H H H H H H H H

F-132 H H H H H H H H

F-133 H H H H H H H H CH3 F-134 H H H H H H H H

F-135 Ph H H H Ph H H H Ph F-136

H H H

H H H Ph F-137 CH3 H H H CH3 H H H Ph F-138 H Ph H H H Ph H H Ph F-139 H

H H H

H H Ph F-140 H CH3 H H H CH3 H H Ph F-141 H H H H H H H H Ph F-142 H H HH H H H H Ph F-143 H H H H H H H H Ph Compound No. X12 X13 X14 X21 X22X23 X24 F-128 X12 and X13 form a fused ring. H H H H H F-129 X12 and X13form a fused ring. Ph Ph H H Ph F-130 X12 and X13 form a fused ring.

H H

F-131 X12 and X13 form a fused ring.

H H

F-132 X12 and X13 form a fused ring.

H H

F-133 X12 and X13 form a fused ring. CH3 CH3 H H CH3 F-134 X12 and X13form a fused ring.

H H

F-135 X12 and X13 form a fused ring. Ph Ph H H Ph F-136 X12 and X13 forma fused ring. Ph Ph H H Ph F-137 X12 and X13 form a fused ring. Ph Ph HH Ph F-138 X12 and X13 form a fused ring. Ph Ph H H Ph F-139 X12 and X13form a fused ring. Ph Ph H H Ph F-140 X12 and X13 form a fused ring. PhPh H H Ph F-141 X12 and X13 form a fused ring. Ph Ph Ph Ph Ph F-142 X12and X13 form a fused ring. Ph Ph

Ph F-143 X12 and X13 form a fused ring. Ph Ph CH3 CH3 Ph Compound No. X2X3 X6 X7 X32 X33 X36 X37 X11 F-144 H H H H H H H H H F-145 H H H H H H HH Ph F-146 H H H H H H H H

F-147 H H H H H H H H

F-148 H H H H H H H H

F-149 H H H H H H H H CH3 F-150 H H H H H H H H

F-151 Ph H H H Ph H H H Ph F-152

H H H

H H H Ph F-153 CH3 H H H CH3 H H H Ph F-154 H Ph H H H Ph H H Ph F-155 H

H H H

H H Ph F-156 H CH3 H H H CH3 H H Ph F-157 H H H H H H H H Ph F-158 H H HH H H H H Ph F-159 H H H H H H H H Ph Compound No. X12 X13 X14 X21 X22X23 X24 F-144 H H H X21 and X22 form a fused ring. X23 and X24 form afused ring. F-145 H H Ph X21 and X22 form a fused ring. X23 and X24 forma fused ring. F-146 H H

X21 and X22 form a fused ring. X23 and X24 form a fused ring. F-147 H H

X21 and X22 form a fused ring. X23 and X24 form a fused ring. F-148 H H

X21 and X22 form a fused ring. X23 and X24 form a fused ring. F-149 H HCH3 X21 and X22 form a fused ring. X23 and X24 form a fused ring. F-150H H

X21 and X22 form a fused ring. X23 and X24 form a fused ring. F-151 H HPh X21 and X22 form a fused ring. X23 and X24 form a fused ring. F-152 HH Ph X21 and X22 form a fused ring. X23 and X24 form a fused ring. F-153H H Ph X21 and X22 form a fused ring. X23 and X24 form a fused ring.F-154 H H Ph X21 and X22 form a fused ring. X23 and X24 form a fusedring. F-155 H H Ph X21 and X22 form a fused ring. X23 and X24 form afused ring. F-156 H H Ph X21 and X22 form a fused ring. X23 and X24 forma fused ring. F-157 Ph Ph Ph X21 and X22 form a fused ring. X23 and X24form a fused ring. F-158

Ph X21 and X22 form a fused ring. X23 and X24 form a fused ring. F-159CH3 CH3 Ph X21 and X22 form a fused ring. X23 and X24 form a fused ring.Compound No. X2 X3 X6 X7 X32 X33 X36 X37 X11       X12 F-160 H H H H H HH H X11 and X12 form a fused ring. F-161 Ph H H H Ph H H H X11 and X12form a fused ring. F-162

H H H

H H H X11 and X12 form a fused ring. F-163 CH3 H H H CH3 H H H X11 andX12 form a fused ring. F-164 H Ph H H H Ph H H X11 and X12 form a fusedring. F-165 H

H H H

H H X11 and X12 form a fused ring. F-166 H CH3 H H H CH3 H H X11 and X12form a fused ring. Compound No. X13 X14 X21 X22 X23 X24 F-160 X13 andX14 form a fused ring. X21 and X22 form a fused ring. X23 and X24 form afused ring. F-161 X13 and X14 form a fused ring. X21 and X22 form afused ring. X23 and X24 form a fused ring. F-162 X13 and X14 form afused ring. X21 and X22 form a fused ring. X23 and X24 form a fusedring. F-163 X13 and X14 form a fused ring. X21 and X22 form a fusedring. X23 and X24 form a fused ring. F-164 X13 and X14 form a fusedring. X21 and X22 form a fused ring. X23 and X24 form a fused ring.F-165 X13 and X14 form a fused ring. X21 and X22 form a fused ring. X23and X24 form a fused ring. F-166 X13 and X14 form a fused ring. X21 andX22 form a fused ring. X23 and X24 form a fused ring. Compound No. X2 X3X6 X7 X32 X33 X36 X37 X11 F-167 H H H H H H H H H F-168 H H H H H H H HPh F-169 H H H H H H H H

F-170 H H H H H H H H

F-171 H H H H H H H H

F-172 H H H H H H H H CH3 F-173 H H H H H H H H

F-174 Ph H H H Ph H H H Ph F-175

H H H

H H H Ph F-176 CH3 H H H CH3 H H H Ph F-177 H Ph H H H Ph H H Ph F-178 H

H H H

H H Ph F-179 H CH3 H H H CH3 H H Ph F-180 H H H H H H H H Ph F-181 H H HH H H H H Ph F-182 H H H H H H H H Ph Compound No. X12 X13 X14 X21 X22X23 X24 F-167 H X13 and X14 form a fused ring. X21 and X22 form a fusedring. H H F-168 H X13 and X14 form a fused ring. X21 and X22 form afused ring. H Ph F-169 H X13 and X14 form a fused ring. X21 and X22 forma fused ring. H

F-170 H X13 and X14 form a fused ring. X21 and X22 form a fused ring. H

F-171 H X13 and X14 form a fused ring. X21 and X22 form a fused ring. H

F-172 H X13 and X14 form a fused ring. X21 and X22 form a fused ring. HCH3 F-173 H X13 and X14 form a fused ring. X21 and X22 form a fusedring. H

F-174 H X13 and X14 form a fused ring. X21 and X22 form a fused ring. HPh F-175 H X13 and X14 form a fused ring. X21 and X22 form a fused ring.H Ph F-176 H X13 and X14 form a fused ring. X21 and X22 form a fusedring. H Ph F-177 H X13 and X14 form a fused ring. X21 and X22 form afused ring. H Ph F-178 H X13 and X14 form a fused ring. X21 and X22 forma fused ring. H Ph F-179 H X13 and X14 form a fused ring. X21 and X22form a fused ring. H Ph F-180 Ph X13 and X14 form a fused ring. X21 andX22 form a fused ring. Ph Ph F-181

X13 and X14 form a fused ring. X21 and X22 form a fused ring.

Ph F-182 CH3 X13 and X14 form a fused ring. X21 and X22 form a fusedring. CH3 Ph Compound No. X2 X3 X6 X7 X32 X33 X36 X37 X11 F-183 H H H HH H H H H F-184 H H H H H H H H Ph F-185 H H H H H H H H

F-186 H H H H H H H H

F-187 H H H H H H H H

F-188 H H H H H H H H CH3 F-189 H H H H H H H H

F-190 Ph H H H Ph H H H Ph F-191

H H H

H H H Ph F-192 CH3 H H H CH3 H H H Ph F-193 H Ph H H H Ph H H Ph F-194 H

H H H

H H Ph F-195 H CH3 H H H CH3 H H Ph F-196 H H H H H H H H Ph F-197 H H HH H H H H Ph F-198 H H H H H H H H Ph Compound No. X12 X13 X14 X21 X22X23 X24 F-183 H X13 and X14 form a fused ring. H H H H F-184 H X13 andX14 form a fused ring. Ph H X23 and X24 form a fused ring. F-185 H X13and X14 form a fused ring.

H X23 and X24 form a fused ring. F-186 H X13 and X14 form a fused ring.

H X23 and X24 form a fused ring. F-187 H X13 and X14 form a fused ring.

H X23 and X24 form a fused ring. F-188 H X13 and X14 form a fused ring.CH3 H X23 and X24 form a fused ring. F-189 H X13 and X14 form a fusedring.

H X23 and X24 form a fused ring. F-190 H X13 and X14 form a fused ring.Ph H X23 and X24 form a fused ring. F-191 H X13 and X14 form a fusedring. Ph H X23 and X24 form a fused ring. F-192 H X13 and X14 form afused ring. Ph H X23 and X24 form a fused ring. F-193 H X13 and X14 forma fused ring. Ph H X23 and X24 form a fused ring. F-194 H X13 and X14form a fused ring. Ph H X23 and X24 form a fused ring. F-195 H X13 andX14 form a fused ring. Ph H X23 and X24 form a fused ring. F-196 Ph X13and X14 form a fused ring. Ph Ph X23 and X24 form a fused ring. F-197

X13 and X14 form a fused ring. Ph

X23 and X24 form a fused ring. F-198 CH3 X13 and X14 form a fused ring.Ph CH3 X23 and X24 form a fused ring.

[0287]

“A and B form a fused ring” in

means

Compound No. X2 = X32 X3 = X33 X6 = X36 X7 = X37 X11 X14 X15 G-1 H H H HH H H G-2 H H H H Ph Ph H G-3 H H H H

H G-4 H H H H

H G-5 H H H H

H G-6 H H H H CH3 CH3 H G-7 H H H H

H G-8 H H H H Ph Ph Ph G-9 H H H H Ph Ph

G-10 H H H H Ph Ph CH3 G-11 H H H H Ph Ph H G-12 H H H H Ph Ph H G-13 HH H H Ph Ph H G-14 Ph H H H Ph Ph H G-15

H H H Ph Ph H G-16 CH3 H H H Ph Ph H Compound No. X16 X17 X18 X21 X24G-1 H H H H H G-2 H H H Ph Ph G-3 H H H

G-4 H H H

G-5 H H H

G-6 H H H CH3 CH3 G-7 H H H

G-8 H H Ph Ph Ph G-9 H H

Ph Ph G-10 H H CH3 Ph Ph G-11 Ph Ph H Ph Ph G-12

H Ph Ph G-13 CH3 CH3 H Ph Ph G-14 H H H Ph Ph G-15 H H H Ph Ph G-16 H HH Ph Ph Compound No. X25 X26 X27 X28 G-1 H H H H G-2 H H H H G-3 H H H HG-4 H H H H G-5 H H H H G-6 H H H H G-7 H H H H G-8 Ph H H Ph G-9

H H

G-10 CH3 H H CH3 G-11 H Ph Ph H G-12 H

H G-13 H CH3 CH3 H G-14 H H H H G-15 H H H H G-16 H H H H Compound No.X2 = X32 X3 = X33 X6 = X36 X7 = X37 X11 X14 X15 X16 X17 G-17 H H H H H HH X16 and X17 form a fused ring. G-18 H H H H Ph Ph H X16 and X17 form afused ring. G-19 H H H H

H X16 and X17 form a fused ring. G-20 H H H H

H X16 and X17 form a fused ring. G-21 H H H H

H X16 and X17 form a fused ring. G-22 H H H H CH3 CH3 H X16 and X17 forma fused ring. G-23 H H H H

H X16 and X17 form a fused ring. G-24 H H H H Ph Ph Ph X16 and X17 forma fused ring. G-25 H H H H Ph Ph

X16 and X17 form a fused ring. G-26 H H H H Ph Ph CH3 X16 and X17 form afused ring. G-27 Ph H H H Ph Ph H X16 and X17 form a fused ring. G-28

H H H Ph Ph H X16 and X17 form a fused ring. G-29 CH3 H H H Ph Ph H X16and X17 form a fused ring. Compound No. X18 X21 X24 X25 X26 X27 X28 G-17H H H H X26 and X27 form a fused ring H G-18 H Ph Ph H X26 and X27 forma fused ring H G-19 H

H X26 and X27 form a fused ring H G-20 H

H X26 and X27 form a fused ring H G-21 H

H X26 and X27 form a fused ring H G-22 H CH3 CH3 H X26 and X27 form afused ring H G-23 H

H X26 and X27 form a fused ring H G-24 Ph Ph Ph Ph X26 and X27 form afused ring H G-25

Ph Ph

X26 and X27 form a fused ring H G-26 CH3 Ph Ph CH3 X26 and X27 form afused ring H G-27 H Ph Ph H X26 and X27 form a fused ring H G-28 H Ph PhH X26 and X27 form a fused ring H G-29 H Ph Ph H X26 and X27 form afused ring H Compound No. X2 = X32 X3 = X33 X6 = X36 X7 = X37 X11 X14X15 G-30 H H H H H H H G-31 H H H H Ph Ph H G-32 H H H H

H G-33 H H H H

H G-34 H H H H

H G-35 H H H H CH3 CH3 H G-36 H H H H

H G-37 H H H H Ph Ph Ph G-38 H H H H Ph Ph

G-39 H H H H Ph Ph CH3 G-40 H H H H Ph Ph H G-41 H H H H Ph Ph H G-42 HH H H Ph Ph H G-43 Ph H H H Ph Ph H G-44

H H H Ph Ph H G-45 CH3 H H H Ph Ph H Compound No. X16       X17 X18 X21X24 X25 G-30 X16 and X17 form a fused ring. H H H H G-31 X16 and X17form a fused ring. H Ph Ph H G-32 X16 and X17 form a fused ring. H

H G-33 X16 and X17 form a fused ring. H

H G-34 X16 and X17 form a fused ring. H

H G-35 X16 and X17 form a fused ring. H CH3 CH3 H G-36 X16 and X17 forma fused ring. H

H G-37 X16 and X17 form a fused ring. Ph Ph Ph Ph G-38 X16 and X17 forma fused ring.

Ph Ph

G-39 X16 and X17 form a fused ring. CH3 Ph Ph CH3 G-40 X16 and X17 forma fused ring. H Ph Ph H G-41 X16 and X17 form a fused ring. H Ph Ph HG-42 X16 and X17 form a fused ring. H Ph Ph H G-43 X16 and X17 form afused ring. H Ph Ph H G-44 X16 and X17 form a fused ring. H Ph Ph H G-45X16 and X17 form a fused ring. H Ph Ph H Compound No. X26 X27 X28 G-30 HH H G-31 H H H G-32 H H H G-33 H H H G-34 H H H G-35 H H H G-36 H H HG-37 H H Ph G-38 H H

G-39 H H CH3 G-40 Ph Ph H G-41

H G-42 CH3 CH3 H G-43 H H H G-44 H H H G-45 H H H Compound No. X2 = X32X3 = X33 X6 = X36 X7 = X37 X11 X14 X15 X16 X17 G-46 H H H H H H X15 andX16 form a fused ring. H G-47 H H H H Ph Ph X15 and X16 form a fusedring. H G-48 H H H H

X15 and X16 form a fused ring. H G-49 H H H H

X15 and X16 form a fused ring. H G-50 H H H H

X15 and X16 form a fused ring. H G-51 H H H H CH3 CH3 X15 and X16 form afused ring. H G-52 H H H H

X15 and X16 form a fused ring. H G-53 H H H H Ph Ph X15 and X16 form afused ring. H G-54 H H H H Ph Ph X15 and X16 form a fused ring. H G-55 HH H H Ph Ph X15 and X16 form a fused ring. H G-56 H H H H Ph Ph X15 andX16 form a fused ring. Ph G-57 H H H H Ph Ph X15 and X16 form a fusedring.

G-58 H H H H Ph Ph X15 and X16 form a fused ring. CH3 G-59 Ph H H H PhPh X15 and X16 form a fused ring. G-60

H H H Ph Ph X15 and X16 form a fused ring. G-61 CH3 H H H Ph Ph X15 andX16 form a fused ring. Compound No. X18 X21 X24 X25 X26 X27 X28 G-46 H HH H H X27 and X28 form a fused ring. G-47 H Ph Ph H H X27 and X28 form afused ring. G-48 H

H H X27 and X28 form a fused ring. G-49 H

H H X27 and X28 form a fused ring. G-50 H

H H X27 and X28 form a fused ring. G-51 H CH3 CH3 H H X27 and X28 form afused ring. G-52 H

H H X27 and X28 form a fused ring. G-53 Ph Ph Ph Ph H X27 and X28 form afused ring. G-54

Ph Ph

H X27 and X28 form a fused ring. G-55 CH3 Ph Ph CH3 H X27 and X28 form afused ring. G-56 H Ph Ph H Ph X27 and X28 form a fused ring. G-57 H PhPh H

X27 and X28 form a fused ring. G-58 H Ph Ph H CH3 X27 and X28 form afused ring. G-59 H Ph Ph H H X27 and X28 form a fused ring. G-60 H Ph PhH H X27 and X28 form a fused ring. G-61 H Ph Ph H H X27 and X28 form afused ring. Compound No. X2 = X32 X3 = X33 X6 = X36 X7 = X37 X11 X14 X15X16 X17 X18 G-62 H H H H H H X15 and X16 form a fused ring. X17 and X18form a fused ring. G-63 H H H H Ph Ph X15 and X16 form a fused ring. X17and X18 form a fused ring. G-64 H H H H

X15 and X16 form a fused ring. X17 and X18 form a fused ring. G-65 H H HH

X15 and X16 form a fused ring. X17 and X18 form a fused ring. G-66 H H HH

X15 and X16 form a fused ring. X17 and X18 form a fused ring. G-67 H H HH CH3 CH3 X15 and X16 form a fused ring. X17 and X18 form a fused ring.G-68 H H H H

X15 and X16 form a fused ring. X17 and X18 form a fused ring. G-69 Ph HH H Ph Ph X15 and X16 form a fused ring. X17 and X18 form a fused ring.G-70

H H H Ph Ph X15 and X16 form a fused ring. X17 and X18 form a fusedring. G-71 CH3 H H H Ph Ph X15 and X16 form a fused ring. X17 and X18form a fused ring. Compound No. X21 X24 X25 X26 X27 X28 G-62 H H X25 andX26 form a fused ring. X27 and X28 form a fused ring. G-63 Ph Ph X25 andX26 form a fused ring. X27 and X28 form a fused ring. G-64

X25 and X26 form a fused ring. X27 and X28 form a fused ring. G-65

X25 and X26 form a fused ring. X27 and X28 form a fused ring. G-66

X25 and X26 form a fused ring. X27 and X28 form a fused ring. G-67 CH3CH3 X25 and X26 form a fused ring. X27 and X28 form a fused ring. G-68

X25 and X26 form a fused ring. X27 and X28 form a fused ring. G-69 Ph PhX25 and X26 form a fused ring. X27 and X28 form a fused ring. G-70 Ph PhX25 and X26 form a fused ring. X27 and X28 form a fused ring. G-71 Ph PhX25 and X26 form a fused ring. X27 and X28 form a fused ring. CompoundNo. X2       X3 X6 X7 X32 X33 X36 X37 X11 = X21 X14 = X24 G-72 X2 and X3form a fused ring. H H H H H H H H G-73 X2 and X3 form a fused ring. H HH H H H Ph Ph G-74 X2 and X3 form a fused ring. H H H H H H

G-75 X2 and X3 form a fused ring. H H H H H H

G-76 X2 and X3 form a fused ring. H H H H H H

G-77 X2 and X3 form a fused ring. H H H H H H CH3 CH3 G-78 X2 and X3form a fused ring. H H H H H H

G-79 X2 and X3 form a fused ring. H H H H H H Ph Ph G-80 X2 and X3 forma fused ring. H H H H H H Ph Ph G-81 X2 and X3 form a fused ring. H H HH H H Ph Ph G-82 X2 and X3 form a fused ring. H H H H H H Ph Ph G-83 X2and X3 form a fused ring. H H H H H H Ph Ph G-84 X2 and X3 form a fusedring. H H H H H H Ph Ph G-85 X2 and X3 form a fused ring. H H Ph H H HPh Ph G-86 X2 and X3 form a fused ring. H H

H H H Ph Ph G-87 X2 and X3 form a fused ring. H H CH3 H H H Ph PhCompound No. X15 = X25 X16 = X26 X17 = X27 X18 = X28 G-72 H H H H G-73 HH H H G-74 H H H H G-75 H H H H G-76 H H H H G-77 H H H H G-78 H H H HG-79 Ph H H Ph G-80

H H

G-81 CH3 H H CH3 G-82 H Ph Ph H G-83 H

H G-84 H CH3 CH3 H G-85 H H G-86 H H G-87 H H Compound No. X2       X3X6 X7 X32       X33 X36 X37 X11 = X21 X14 = X24 G-88 X2 and X3 form afused ring. H H X32 and X33 form a fused ring. H H H H G-89 X2 and X3form a fused ring. H H X32 and X33 form a fused ring. H H Ph Ph G-90 X2and X3 form a fused ring. H H X32 and X33 form a fused ring. H H

G-91 X2 and X3 form a fused ring. H H X32 and X33 form a fused ring. H H

G-92 X2 and X3 form a fused ring. H H X32 and X33 form a fused ring. H H

G-93 X2 and X3 form a fused ring. H H X32 and X33 form a fused ring. H HCH3 CH3 G-94 X2 and X3 form a fused ring. H H X32 and X33 form a fusedring. H H

G-95 X2 and X3 form a fused ring. H H X32 and X33 form a fused ring. H HPh Ph G-96 X2 and X3 form a fused ring. H H X32 and X33 form a fusedring. H H Ph Ph G-97 X2 and X3 form a fused ring. H H X32 and X33 form afused ring. H H Ph Ph G-98 X2 and X3 form a fused ring. H H X32 and X33form a fused ring. H H Ph Ph G-99 X2 and X3 form a fused ring. H H X32and X33 form a fused ring. H H Ph Ph G-100 X2 and X3 form a fused ring.H H X32 and X33 form a fused ring. H H Ph Ph Compound No. X15 = X25 X16= X26 X17 = X27 X18 = X28 G-88 H H H H G-89 H H H H G-90 H H H H G-91 HH H H G-92 H H H H G-93 H H H H G-94 H H H H G-95 Ph H H Ph G-96

H H

G-97 CH3 H H CH3 G-98 H Ph Ph H G-99 H

H G-100 H CH3 CH3 H

[0288]

“A and B form a fused ring” in

means

Compound No. X2 X3 X6 X7 X32       X33 X36 X37 X34 = X35 X11 X14 H-1 H HH H X2 and X3 form a fused ring. H H H H H H-2 H H H H X2 and X3 form afused ring. H H H Ph Ph H-3 H H H H X2 and X3 form a fused ring. H H H

H-4 H H H H X2 and X3 form a fused ring. H H H

H-5 H H H H X2 and X3 form a fused ring. H H H

H-6 H H H H X2 and X3 form a fused ring. H H H CH3 CH3 H-7 H H H H X2and X3 form a fused ring. H H H

H-8 H H H H X2 and X3 form a fused ring. H H H Ph Ph H-9 H H H H X2 andX3 form a fused ring. H H H Ph Ph H-10 H H H H X2 and X3 form a fusedring. H H H Ph Ph H-11 H H H H X2 and X3 form a fused ring. H H H Ph PhH-12 H H H H X2 and X3 form a fused ring. H H H Ph Ph H-13 H H H H X2and X3 form a fused ring. H H H Ph Ph H-14 Ph H H H X2 and X3 form afused ring. H H H Ph Ph H-15

H H H X2 and X3 form a fused ring. H H H Ph Ph H-16 CH3 H H H X2 and X3form a fused ring. H H H Ph Ph Compound No. X15 X16 X17 X18 H-1 H H H HH-2 H H H H H-3 H H H H H-4 H H H H H-5 H H H H H-6 H H H H H-7 H H H HH-8 Ph H H Ph H-9

H H

H-10 CH3 H H CH3 H-11 H Ph Ph H H-12 H

H H-13 H CH3 CH3 H H-14 H H H H H-15 H H H H H-16 H H H H Compound No.X2 = X32 X3 = X33 X6 = X36 X7 = X37 X34 = X35 X11 X14 X15 H-17 H H H H HH H H H-18 H H H H H Ph Ph H H-19 H H H H H

H H-20 H H H H H

H H-21 H H H H H

H H-22 H H H H H CH3 CH3 H H-23 H H H H H

H H-24 H H H H H Ph Ph Ph H-25 H H H H H Ph Ph

H-26 H H H H H Ph Ph CH3 H-27 H H H H H Ph Ph H H-28 H H H H H Ph Ph HH-29 H H H H H Ph Ph H H-30 Ph H H H H Ph Ph H H-31

H H H H Ph Ph H H-32 CH3 H H H H Ph Ph H Compound No. X16 X17 X18 H-17 HH H H-18 H H H H-19 H H H H-20 H H H H-21 H H H H-22 H H H H-23 H H HH-24 H H Ph H-25 H H

H-26 H H CH3 H-27 Ph Ph H H-28

H H-29 CH3 CH3 H H-30 H H H H-31 H H H H-32 H H H Compound No. X2 = X32X3 = X33 X6 = X36 X7 = X37 X34 = X35 X11 X14 H-33 H H H H H H H-34 H H HH Ph Ph H-35 H H H H

H-36 H H H H

H-37 H H H H

H-38 H H H H CH3 CH3 H-39 H H H H H

H-40 H H H H H Ph Ph H-41 H H H H H Ph Ph H-42 H H H H H Ph Ph H-43 H HH H H Ph Ph H-44 H H H H H Ph Ph H-45 H H H H H Ph Ph H-46 Ph H H H H PhPh H-47

H H H H Ph Ph H-48 CH3 H H H H Ph Ph Compound No. X15 X16 X17 X18 H-33X15 and X16 form a fused ring. H H H-34 X15 and X16 form a fused ring. HH H-35 X15 and X16 form a fused ring. H H H-36 X15 and X16 form a fusedring. H H H-37 X15 and X16 form a fused ring. H H H-38 X15 and X16 forma fused ring. H H H-39 X15 and X16 form a fused ring. H H H-40 X15 andX16 form a fused ring. H Ph H-41 X15 and X16 form a fused ring. H

H-42 X15 and X16 form a fused ring. H CH3 H-43 X15 and X16 form a fusedring. Ph H H-44 X15 and X16 form a fused ring.

H H-45 X15 and X16 form a fused ring. CH3 H H-46 X15 and X16 form afused ring. H H-47 X15 and X16 form a fused ring. H H-48 X15 and X16form a fused ring. H Compound No. X2 = X32 X3 = X33 X6 = X36 X7 = X37X34 = X35 X11 X14 H-49 H H H H H H H H-50 H H H H H Ph Ph H-51 H H H H H

H-52 H H H H H

H-53 H H H H H

H-54 H H H H H CH3 CH3 H-55 H H H H H

H-56 H H H H H Ph Ph H-57 H H H H H Ph Ph H-58 H H H H H Ph Ph H-59 H HH H H Ph Ph H-60 H H H H H Ph Ph H-61 H H H H H Ph Ph H-62 Ph H H H H PhPh H-63

H H H H Ph Ph H-64 CH3 H H H H Ph Ph Compound No. X15 X16 X17 X18 H-49 HX16 and X17 form a fused ring. H H-50 H X16 and X17 form a fused ring. HH-51 H X16 and X17 form a fused ring. H H-52 H X16 and X17 form a fusedring. H H-53 H X16 and X17 form a fused ring. H H-54 H X16 and X17 forma fused ring. H H-55 H X16 and X17 form a fused ring. H H-56 Ph X16 andX17 form a fused ring. Ph H-57

X16 and X17 form a fused ring.

H-58 CH3 X16 and X17 form a fused ring. CH3 H-59 H X16 and X17 form afused ring. H H-60 H X16 and X17 form a fused ring. H H-61 H X16 and X17form a fused ring. H H-62 H X16 and X17 form a fused ring. H H-63 H X16and X17 form a fused ring. H H-64 H X16 and X17 form a fused ring. HCompound No. X2 = X32 X3 = X33 X6 = X36 X7 = X37 X34 = X35 X11 X14 H-65H H H H H H H H-66 H H H H H Ph Ph H-67 H H H H H

H-68 H H H H H

H-69 H H H H H

H-70 H H H H H CH3 CH3 H-71 H H H H H

H-72 Ph H H H H Ph Ph H-73

H H H H Ph Ph H-74 CH3 H H H H Ph Ph Compound No. X15       X16 X17      X18 H-65 X15 and X16 form a fused ring. X17 and X18 form a fusedring. H-66 X15 and X16 form a fused ring. X17 and X18 form a fused ring.H-67 X15 and X16 form a fused ring. X17 and X18 form a fused ring. H-68X15 and X16 form a fused ring. X17 and X18 form a fused ring. H-69 X15and X16 form a fused ring. X17 and X18 form a fused ring. H-70 X15 andX16 form a fused ring. X17 and X18 form a fused ring. H-71 X15 and X16form a fused ring. X17 and X18 form a fused ring. H-72 X15 and X16 forma fused ring. X17 and X18 form a fused ring. H-73 X15 and X16 form afused ring. X17 and X18 form a fused ring. H-74 X15 and X16 form a fusedring. X17 and X18 form a fused ring.

“A and B form a fused ring” in

means

Compound No. X2       X3 X6 X7 X32       X33 X36 X37 X34 = X35 X11 X14H-75 X2 and X3 form a fused ring. H H X32 and X33 form a fused ring. H HH H H H-76 X2 and X4 form a fused ring. H H X32 and X33 form a fusedring. H H H Ph Ph H-77 X2 and X5 form a fused ring. H H X32 and X33 forma fused ring. H H H

H-78 X2 and X6 form a fused ring. H H X32 and X33 form a fused ring. H HH

H-79 X2 and X7 form a fused ring. H H X32 and X33 form a fused ring. H HH

H-80 X2 and X8 form a fused ring. H H X32 and X33 form a fused ring. H HH CH3 CH3 H-81 X2 and X9 form a fused ring. H H X32 and X33 form a fusedring. H H H

H-82 X2 and X10 form a fused ring. H H X32 and X33 form a fused ring. HH H Ph Ph H-83 X2 and X11 form a fused ring. H H X32 and X33 form afused ring. H H H Ph Ph H-84 X2 and X12 form a fused ring. H H X32 andX33 form a fused ring. H H H Ph Ph H-85 X2 and X13 form a fused ring. HH X32 and X33 form a fused ring. H H H Ph Ph H-86 X2 and X14 form afused ring. H H X32 and X33 form a fused ring. H H H Ph Ph H-87 X2 andX15 form a fused ring. H H X32 and X33 form a fused ring. H H H Ph PhCompound No. X15 X16 X17 X18 H-75 H H H H H-76 H H H H H-77 H H H H H-78H H H H H-79 H H H H H-80 H H H H H-81 H H H H H-82 Ph H H Ph H-83

H H

H-84 CH3 H H CH3 H-85 H Ph Ph H H-86 H

H H-87 H CH3 CH3 H

“A and B form a fused ring” in

means

Compound No. X2       X3 X6 X7 X32 X33 X36 X37 X34 = X35 X11 X14 H-88 X2and X3 form a fused ring. H H H H H H H H H H-89 X2 and X4 form a fusedring. H H H H H H H Ph Ph H-90 X2 and X5 form a fused ring. H H H H H HH

H-91 X2 and X6 form a fused ring. H H H H H H H

H-92 X2 and X7 form a fused ring. H H H H H H H

H-93 X2 and X8 form a fused ring. H H H H H H H CH3 CH3 H-94 X2 and X9form a fused ring. H H H H H H H

H-95 X2 and X10 form a fused ring. H H H H H H H Ph Ph H-96 X2 and X11form a fused ring. H H H H H H H Ph Ph H-97 X2 and X12 form a fusedring. H H H H H H H Ph Ph H-98 X2 and X13 form a fused ring. H H H H H HH Ph Ph H-99 X2 and X14 form a fused ring. H H H H H H H Ph Ph H-100 X2and X15 form a fused ring. H H H H H H H Ph Ph H-101 X2 and X16 form afused ring. H H Ph H H H H Ph Ph H-102 X2 and X17 form a fused ring. H H

H H H H Ph Ph H-103 X2 and X18 form a fused ring. H H CH3 H H H H Ph PhCompound No. X15 X16 X17 X18 H-88 H H H H H-89 H H H H H-90 H H H H H-91H H H H H-92 H H H H H-93 H H H H H-94 H H H H H-95 Ph H H Ph H-96

H H

H-97 CH3 H H CH3 H-98 H Ph Ph H H-99 H

H H-100 H CH3 CH3 H H-101 H H H H H-102 H H H H H-103 H H H H

[0289]

“A and B form a fused ring” in

means

Compound No. X2 X3 X6 X7 X32 X33 X34 = X35 X36 X37 I-1 H H H H H H H H HI-2 H H H H H H H H H I-3 H H H H H H H H H I-4 H H H H H H H H H I-5 HH H H H H H H H I-6 H H H H H H H H H I-7 H H H H H H H H H I-8 Ph H H HPh H H H H I-9

H H H

H H H H I-10 CH3 H H H CH3 H H H H I-11 H Ph H H H Ph H H H I-12 H

H H H

H H H I-13 H CH3 H H H CH3 H H H I-14 H H H H H H H H H I-15 H H H H H HH H H I-16 H H H H H H H H H I-17 H H H H H H H H H I-18 H H H H H H H HH I-19 H H H H H H H H H I-20 H H H H H H H H H I-21 H H H H H H H H HI-22 H H H H H H H H H I-23 H H H H H H H H H I-24 Ph H H H Ph H H H HI-25

H H H

H H H H I-26 CH3 H H H CH3 H H H H I-27 H Ph H H H Ph H H H I-28 H

H H H

H H H I-29 H CH3 H H H CH3 H H H I-30 H H H H H H H H H I-31 H H H H H HH H H I-32 H H H H H H H H H Compound No. X11 X12 X13 X14 I-1 H H H HI-2 Ph H H Ph I-3

H H

I-4

H H

I-5

H H

I-6 CH3 H H CH3 I-7

H H

I-8 Ph H H Ph I-9 Ph H H Ph I-10 Ph H H Ph I-11 Ph H H Ph I-12 Ph H H PhI-13 Ph H H Ph I-14 Ph Ph Ph Ph I-15 Ph

Ph I-16 Ph CH3 CH3 Ph I-17 H H X13 and X14 form a fused ring. I-18 Ph HX13 and X14 form a fused ring. I-19

H X13 and X14 form a fused ring. I-20

H X13 and X14 form a fused ring. I-21

H X13 and X14 form a fused ring. I-22 CH3 H X13 and X14 form a fusedring. I-23

H X13 and X14 form a fused ring. I-24 Ph H X13 and X14 form a fusedring. I-25 Ph H X13 and X14 form a fused ring. I-26 Ph H X13 and X14form a fused ring. I-27 Ph H X13 and X14 form a fused ring. I-28 Ph HX13 and X14 form a fused ring. I-29 Ph H X13 and X14 form a fused ring.I-30 Ph Ph X13 and X14 form a fused ring. I-31 Ph

X13 and X14 form a fused ring. I-32 Ph CH3 X13 and X14 form a fusedring. Compound No. X2 X3 X6 X7 X32 X33 X36 X37 I-33 H H H H H H H H I-34Ph H H H Ph H H H I-35

H H H

H H H I-36 CH3 H H H CH3 H H H I-37 H Ph H H H Ph H H I-38 H

H H H

H H I-39 H CH3 H H H CH3 H H Compound No. X11       X12 X13       X14I-33 X11 and X12 form a fused ring. X13 and X14 form a fused ring. I-34X11 and X12 form a fused ring. X13 and X14 form a fused ring. I-35 X11and X12 form a fused ring. X13 and X14 form a fused ring. I-36 X11 andX12 form a fused ring. X13 and X14 form a fused ring. I-37 X11 and X12form a fused ring. X13 and X14 form a fused ring. I-38 X11 and X12 forma fused ring. X13 and X14 form a fused ring. I-39 X11 and X12 form afused ring. X13 and X14 form a fused ring. Compound No. X2       X3 X6X7 X32 X33 X34 = X35 X36 X37 X11 I-40 X2 and X3 form a fused ring. H H HH H H H H I-41 X2 and X3 form a fused ring. H H H H H H H Ph I-42 X2 andX3 form a fused ring. H H H H H H H

I-43 X2 and X3 form a fused ring. H H H H H H H

I-44 X2 and X3 form a fused ring. H H H H H H H

I-45 X2 and X3 form a fused ring. H H H H H H H CH3 I-46 X2 and X3 forma fused ring. H H H H H H H

I-47 X2 and X3 form a fused ring. H H Ph H H H H Ph I-48 X2 and X3 forma fused ring. H H

H H H H Ph I-49 X2 and X3 form a fused ring. H H CH3 H H H H Ph I-50 X2and X3 form a fused ring. H H H Ph H H H Ph I-51 X2 and X3 form a fusedring. H H H

H H H Ph I-52 X2 and X3 form a fused ring. H H H CH3 H H H Ph I-53 X2and X3 form a fused ring. H H H H H H H Ph I-54 X2 and X3 form a fusedring. H H H H H H H Ph I-55 X2 and X3 form a fused ring. H H H H H H HPh Compound No. X12 X13 X14 I-40 H H H I-41 H H Ph I-42 H H

I-43 H H

I-44 H H

I-45 H H CH3 I-46 H H

I-47 H H Ph I-48 H H Ph I-49 H H Ph I-50 H H Ph I-51 H H Ph I-52 H H PhI-53 Ph Ph Ph I-54

Ph I-55 CH3 CH3 Ph Compound No. X2 X3 X6 X7 X32       X33 X34 = X35 X36X37 X11 I-56 H H H H X32 and X33 form a fused ring. H H H H I-57 H H H HX32 and X33 form a fused ring. H H H Ph I-58 H H H H X32 and X33 form afused ring. H H H

I-59 H H H H X32 and X33 form a fused ring. H H H

I-60 H H H H X32 and X33 form a fused ring. H H H

I-61 H H H H X32 and X33 form a fused ring. H H H CH3 I-62 H H H H X32and X33 form a fused ring. H H H

I-63 Ph H H H X32 and X33 form a fused ring. H H H Ph I-64

H H H X32 and X33 form a fused ring. H H H Ph I-65 CH3 H H H X32 and X33form a fused ring. H H H Ph I-66 H H H H X32 and X33 form a fused ring.H H H Ph I-67 H H H H X32 and X33 form a fused ring. H H H Ph I-68 H H HH X32 and X33 form a fused ring. H H H Ph Compound No. X12 X13 X14 I-56H H H I-57 H H Ph I-58 H H

I-59 H H

I-60 H H

I-61 H H CH3 I-62 H H

I-63 H H Ph I-64 H H Ph I-65 H H Ph I-66 Ph Ph Ph I-67

Ph I-68 CH3 CH3 Ph Compound No. X2       X3 X6 X7 X32       X33 X34 =X35 X36 X37 X11 I-69 X2 and X3 form a fused ring. H H X32 and X33 form afused ring. H H H H I-70 X2 and X3 form a fused ring. H H X32 and X33form a fused ring. H H H Ph I-71 X2 and X3 form a fused ring. H H X32and X33 form a fused ring. H H H

I-72 X2 and X3 form a fused ring. H H X32 and X33 form a fused ring. H HH

I-73 X2 and X3 form a fused ring. H H X32 and X33 form a fused ring. H HH

I-74 X2 and X3 form a fused ring. H H X32 and X33 form a fused ring. H HH CH3 I-75 X2 and X3 form a fused ring. H H X32 and X33 form a fusedring. H H H

I-76 X2 and X3 form a fused ring. H H X32 and X33 form a fused ring. H HH Ph I-77 X2 and X3 form a fused ring. H H X32 and X33 form a fusedring. H H H Ph I-78 X2 and X3 form a fused ring. H H X32 and X33 form afused ring. H H H Ph Compound No. X12 X13 X14 I-69 H H H I-70 H H PhI-71 H H

I-72 H H

I-73 H H

I-74 H H CH3 I-75 H H

I-76 Ph Ph Ph I-77

Ph I-78 CH3 CH3 Ph Compound No. X2      X3 X6 X7 X32 X33 X34 = X35 X36X37 I-79 X2 and X3 form a fused ring. H H H H H H H I-80 X2 and X3 forma fused ring. H H H H H H H I-81 X2 and X3 form a fused ring. H H H H HH H I-82 X2 and X3 form a fused ring. H H H H H H H I-83 X2 and X3 forma fused ring. H H H H H H H I-84 X2 and X3 form a fused ring. H H H H HH H I-85 X2 and X3 form a fused ring. H H H H H H H I-86 X2 and X3 forma fused ring. H H Ph H H H H I-87 X2 and X3 form a fused ring. H H

H H H H I-88 X2 and X3 form a fused ring. H H CH3 H H H H I-89 X2 and X3form a fused ring. H H H Ph H H H I-90 X2 and X3 form a fused ring. H HH

H H H I-91 X2 and X3 form a fused ring. H H H CH3 H H H I-92 X2 and X3form a fused ring. H H H H H H H I-93 X2 and X3 form a fused ring. H H HH H H H I-94 X2 and X3 form a fused ring. H H H H H H H Compound No. X11X12 X13 X14 I-79 H H X13 and X14 form a fused ring. I-80 Ph H X13 andX14 form a fused ring. I-81

H X13 and X14 form a fused ring. I-82

H X13 and X14 form a fused ring. I-83

H X13 and X14 form a fused ring. I-84 CH3 H X13 and X14 form a fusedring. I-85

H X13 and X14 form a fused ring. I-86 Ph H X13 and X14 form a fusedring. I-87 Ph H X13 and X14 form a fused ring. I-88 Ph H X13 and X14form a fused ring. I-89 Ph H X13 and X14 form a fused ring. I-90 Ph HX13 and X14 form a fused ring. I-91 Ph H X13 and X14 form a fused ring.I-92 Ph Ph X13 and X14 form a fused ring. I-93 Ph

X13 and X14 form a fused ring. I-94 Ph CH3 X13 and X14 form a fusedring.

“A and B form a fused ring” in

means

Compound No. X2       X3 X6 X7 X32       X33 X34 = X35 X36 X37 I-95 X2and X3 form a fused ring. H H X32 and X33 form a fused ring. H H H I-96X2 and X3 form a fused ring. H H X32 and X33 form a fused ring. H H HI-97 X2 and X3 form a fused ring. H H X32 and X33 form a fused ring. H HH I-98 X2 and X3 form a fused ring. H H X32 and X33 form a fused ring. HH H I-99 X2 and X3 form a fused ring. H H X32 and X33 form a fused ring.H H H I-100 X2 and X3 form a fused ring. H H X32 and X33 form a fusedring. H H H I-101 X2 and X3 form a fused ring. H H X32 and X33 form afused ring. H H H I-102 X2 and X3 form a fused ring. H H X32 and X33form a fused ring. H H H I-103 X2 and X3 form a fused ring. H H X32 andX33 form a fused ring. H H H I-104 X2 and X3 form a fused ring. H H X32and X33 form a fused ring. H H H Compound No. X11       X12 X13 X14 I-95X11 and X12 form a fused ring. H I-96 X11 and X12 form a fused ring. PhI-97 X11 and X12 form a fused ring.

I-98 X11 and X12 form a fused ring.

I-99 X11 and X12 form a fused ring.

I-100 X11 and X12 form a fused ring. CH3 I-101 X11 and X12 form a fusedring.

I-102 X11 and X12 form a fused ring. Ph Ph I-103 X11 and X12 form afused ring.

Ph I-104 X11 and X12 form a fused ring. CH4 Ph

“A and B form a fused ring” in

means

Compound No. X2 X3 X6 X7 X32       X33 X34 = X35 X36       X37 X11 I-105H H H H X32 and X33 form a fused ring. H X36 and X37 form a fused ring.H I-106 H H H H X32 and X33 form a fused ring. H X36 and X37 form afused ring. Ph I-107 H H H H X32 and X33 form a fused ring. H X36 andX37 form a fused ring.

I-108 H H H H X32 and X33 form a fused ring. H X36 and X37 form a fusedring.

I-109 H H H H X32 and X33 form a fused ring. H X36 and X37 form a fusedring.

I-110 H H H H X32 and X33 form a fused ring. H X36 and X37 form a fusedring. CH3 I-111 H H H H X32 and X33 form a fused ring. H X36 and X37form a fused ring.

I-112 H Ph H H X32 and X33 form a fused ring. H X36 and X37 form a fusedring. Ph I-113 H

H H X32 and X33 form a fused ring. H X36 and X37 form a fused ring. PhI-114 H CH3 H H X32 and X33 form a fused ring. H X36 and X37 form afused ring. Ph I-115 H H H H X32 and X33 form a fused ring. H X36 andX37 form a fused ring. Ph I-116 H H H H X32 and X33 form a fused ring. HX36 and X37 form a fused ring. Ph I-117 H H H H X32 and X33 forms fusedring. H X36 and X37 form a fused ring. Ph Compound No. X12 X13 X14 I-105H H H I-106 H H Ph I-107 H H

I-108 H H

I-109 H H

I-110 H H CH3 I-111 H H

I-112 H H Ph I-113 H H Ph I-114 H H Ph I-115 Ph Ph Ph I-116

Ph I-117 CH3 CH3 Ph Compound No. X2       X3 X6       X7 X32 X33 X34 =X35 X36 X37 I-118 X2 and X3 form a fused ring. X6 and X7 form a fusedring. H H H H H I-119 X2 and X3 form a fused ring. X6 and X7 form afused ring. H H H H H I-120 X2 and X3 form a fused ring. X6 and X7 forma fused ring. H H H H H I-121 X2 and X3 form a fused ring. X6 and X7form a fused ring. H H H H H I-122 X2 and X3 form a fused ring. X6 andX7 form a fused ring. H H H H H I-123 X2 and X3 form a fused ring. X6and X7 form a fused ring. H H H H H I-124 X2 and X3 form a fused ring.X6 and X7 form a fused ring. H H H H H I-125 X2 and X3 form a fusedring. X6 and X7 form a fused ring. Ph H H H H I-126 X2 and X3 form afused ring. X6 and X7 form a fused ring.

H H H H I-127 X2 and X3 form a fused ring. X6 and X7 form a fused ring.CH3 H H H H I-128 X2 and X3 form a fused ring. X6 and X7 form a fusedring. H Ph H H H I-129 X2 and X3 form a fused ring. X6 and X7 form afused ring. H

H H H I-130 X2 and X3 form a fused ring. X6 and X7 form a fused ring. HCH3 H H H I-131 X2 and X3 form a fused ring. X6 and X7 form a fusedring. H H H H H I-132 X2 and X3 form a fused ring. X6 and X7 form afused ring. H H H H H I-133 X2 and X3 form a fused ring. X6 and X7 forma fused ring. H H H H H Compound No. X11 X12 X13 X14 I-118 H H H H I-119Ph H H Ph I-120

H H

I-121

H H

I-122

H H

I-123 CH3 H H CH3 I-124

H H

I-125 Ph H H Ph I-126 Ph H H Ph I-127 Ph H H Ph I-128 Ph H H Ph I-129 PhH H Ph I-130 Ph H H Ph I-131 Ph Ph Ph Ph I-132 Ph

Ph I-133 Ph CH3 CH3 Ph

[0290]

J-1 J-2

J-3 J-4

J-5 J-6

J-7 J-8

J-9 J-10 J-11

J-12 J-13

J-14 J-15 J-16

J-17 J-18 J-19

J-20 J-21 J-22

J-23 J-24

J-25 J-26 J-27

J-28 J-29

J-30 J-31

J-32 J-33 J-34

J-35 J-36 J-37

J-38 J-39

J-40 J-41

J-42 J-43

J-44 J-45

J-46

[0291] The above dopants, for example, the compounds of formula (VI) canbe produced, for example, by the method described in J. Amer. Chem.Soc., 118, 2374 (1996). Specifically, as shown by the following scheme,the end compound can be produced by reacting a compound of formula (2)with a compound of formula (3) in the presence of aluminumchloride/sodium chloride, cobalt fluoride or thallium trifluoroacetate.

[0292] It is noted that the fluoranthene derivatives of formulas (V),(2) and (3), can be produced, for example, by the method described in J.Amer. Chem. Soc., 118, 2374 (1996). Specifically, as shown by thefollowing scheme, the end compound can be produced by reacting acompound of formula (4) with a compound of formula (5).

[0293] Once the skeleton of formula (VI) is formed, exchange ofsubstituents is effected by a conventional method, obtaining a compoundhaving the desired substituent(s).

[0294] The compounds of formula (VI) are preferably compounds,dibenzo[f,f′]diindeno[1,2,3-cd:1′,2′,3′-lm]perylene derivatives in thefollowing formula (VI′).

[0295] In formula (VI′), X₁ to X₄₄ are as defined for X₁ to X₂₀ informula (VI).

[0296] Preferably, X₁ to X₂₀ in formula (VI) and X₁ to X₄₄ in formula(VI′) are independently selected from among substituted or unsubstitutedaryl, alkyl, alkenyl, alkoxy and aryloxy radicals.

[0297] Further preferably, at least one of X₁ to X₂₀ in formula (VI) andX₁ to X₄₄ in formula (VI′) is an ortho-substituted phenyl radical. Evenmore preferably, in formula (VI) or (VI′), either one or both of X₁ andX₄ and/or either one or both of X₁₁ and X₁₄ are ortho-substituted phenylradicals. The introduction of a substituent at the ortho-position holdsdown the propensity for the compound to decompose upon sublimationpurification and improves fluorescence.

[0298] The use of the ortho-substituted compound is effective forincreasing the fluorescent luminance and holding down the concentrationquenching of the EL device, thereby spreading the margin of the ELdopant and improving the freedom of design.

[0299] The introduction of an ortho-substituted phenyl group has severaladvantages. The ortho-substituted phenyl group introduced makes itpossible to control the association of the perylene skeleton by virtueof its steric hindrance, to improve the solubility in solvents and topurify the compound to a high purity. For the same reason, sublimationpurification becomes possible at a lower temperature and entails littledecomposition. This is also advantageous in obtaining a high puritymaterial. Using such a pure material, an organic EL device having a highemission efficiency is obtainable because the deactivation of excitonsby impurities is minimized. Another reason accounting for the highefficiency is that the association between similar or distinct moleculesin the light emitting layer is suppressed whereby concentrationquenching is restrained.

[0300] Preferred examples of the compound of formula (VI′) are givenbelow.

[0301] The diindeno[1,2,3-cd:1′,2′,3′-lm]perylene derivative shouldpreferably have a vibration structure in both an excitation spectrum anda fluorescence spectrum. The presence of such a vibration structure isascertainable by the appearance of two or more peaks in each of thespectra.

[0302] More preferably, a host material obtained by doping theindenoperylene derivative has such a vibration structure.

[0303] The possession of a vibration structure leads to the manufactureof an organic EL device having improved temperature characteristics.

[0304] It is believed that a drop of EL luminous efficiency bytemperature is due to thermal relaxation entailing a change ofconformation in the excited state. Once a change of conformation in theexcited state occurs, the overlap of molecular orbital function betweenthe ground state and the excited state changes so that the fluorescencespectrum does not become a mirror image of the absorption spectrum. Thefluorescence spectrum of a compound which can take a plurality ofconformations in the excited state is the total of various vibrationstructures and thus becomes a broad spectrum apparently free of avibration structure.

[0305] Accordingly, an organic compound which exhibits a vibrationstructure in the fluorescence spectrum and specifically, a compoundwhose vibration structure is a mirror image of the absorption spectrumexperiences a minimal change of conformation in the excited state andtherefore, when used as a luminescent material in an organic EL device,enables to produce a device having improved temperature characteristicsas demonstrated by a minimal drop of EL luminous efficiency bytemperature during driving.

[0306] For the same reason as above, the organic compound shouldpreferably have a Stokes shift of up to 0.1 eV, especially up to 0.05eV. The lower limit of Stokes shift is not critical although it isusually about 0.01 eV.

[0307] Another factor that governs the temperature characteristics of anorganic EL device is the thermal excitation of carriers from the traplevel. Especially in a doped light emitting layer, the dopant creates atrap level. Upon a temperature change, the hopping probability ofcarriers by thermal excitation changes. This sometimes results inchanges of the carrier balance in the light emitting layer, leading totemperature dependent characteristics with a high efficiency. Incontrast, the device of the invention has a minimized thermal change ofthe trapping of the light emitting layer, that is, minimized temperaturedependence with a high efficiency.

[0308] In a preferred embodiment, the host material, especially at leastone of the organic compounds of formulas (I) to (IV), in a lightemitting layer has a greater electron affinity than an electrontransporting layer and/or a hole transporting layer. If the hostmaterial in a light emitting layer has a greater electron affinity thanan electron transporting layer and/or a hole transporting layer, theinjection efficiency of electrons into the light emitting layerincreases and electrons are blocked at the hole transporting layerinterface, leading to an improvement in luminous efficiency and hence,device lifetime.

[0309] Others

[0310] The light emitting layer containing the host material and thedopant according to the invention has functions of injecting holes andelectrons, transporting them, and recombining holes and electrons tocreate excitons. The use of relatively electronically neutral compoundsin the light emitting layer in addition to the compounds of theinvention enables easy and well-balanced injection and transportation ofelectrons and holes.

[0311] The host material may be used alone or in admixture of two ormore. When a mixture of two or more host materials is used, the mixratio is not critical. In a preferred embodiment, the light emittinglayer contains 80 to 99.9%, more preferably 90 to 99.9%, even morepreferably 95.0 to 99.5% by weight of the host material.

[0312] The thickness of the light emitting layer preferably ranges fromthe thickness corresponding to a single molecule layer to less than thethickness of an organic compound layer, for example, preferably from 1to 85 nm, more preferably 5 to 60 nm, most preferably 5 to 50 nm.

[0313] Preferably the mix layer is formed by a co-deposition process ofevaporating the compounds from distinct sources. If both the compoundshave equal or very close vapor pressure or evaporation temperature, theymay be pre-mixed in a common evaporation boat, from which they areevaporated together. The mix layer is preferably a uniform mixture ofboth the compounds although the compounds can be present in island form.The light emitting layer is generally formed to a predeterminedthickness by evaporating an organic fluorescent material or coating adispersion thereof in a resin binder.

[0314] One exemplary construction of the organic EL light emittingdevice fabricated using the inventive compounds has on a substrate, ahole injecting electrode, a hole injecting and transporting layer, alight emitting and electron injecting and transporting layer, and anelectron injecting electrode in the described order. If desired, aprotective electrode, an auxiliary electrode and a sealing layer areprovided on the electron injecting electrode.

[0315] The organic EL device of the invention is not limited to theabove exemplary construction and may have various other constructions.In another exemplary construction, the light emitting layer is providedsingly and an electron injecting and transporting layer is interposedbetween the light emitting layer and the electron injecting electrode.Also, the light emitting layer may be mixed with the hole injecting andtransporting layer, if desired.

[0316] The thicknesses of the light emitting layer, hole injecting andtransporting layer, and electron injecting and transporting layer arenot critical and vary with a particular formation technique. Usually asingle layer is about 5 to 500 nm thick, especially about 10 to 300 nmthick.

[0317] The thicknesses of the hole injecting and transporting layer andelectron injecting and transporting layer are equal to or range from{fraction (1/10)} to 10 times the thickness of the light emitting layeralthough they depend on the design of a recombination/light emittingregion. When the electron or hole injecting and transporting layer isdivided into an injecting layer and a transporting layer, preferably theinjecting layer is at least 1 nm thick and the transporting layer is atleast 1 nm thick. The upper limit of thickness is generally about 500 nmfor the injecting layer and about 500 nm for the transporting layer. Thesame applies when two injecting and transporting layers are provided.

[0318] The hole injecting and transporting layer has functions offacilitating injection of holes from the hole injecting electrode,transporting them stably, and blocking electrons. The electron injectingand transporting layer has functions of facilitating injection ofelectrons from the electron injecting electrode, transporting themstably, and blocking holes. These layers are effective for increasingthe number of holes and electrons injected into the light emitting layerand confining holes and electrons therein for optimizing therecombination region to improve light emission efficiency.

[0319] In the hole injecting and transporting layer, there may be usedvarious organic compounds as described, for example, in JP-A 63-295695,2-191694, 3-792, 5-234681, 5-239455, 5-299174, 7-126225, 7-126226, and8-100172, and EPO 650955A1. Exemplary are tetraarylbenzidine compounds(triaryldiamines or triphenyldiamines: TPD), aromatic tertiary amines,hydrazone derivatives, carbazole derivatives, triazole derivatives,imidazole derivatives, oxadiazole derivatives having an amino group, andpolythiophenes. Two or more of these compounds may be used, and on suchcombined use, they may be formed as separate layers or mixed.

[0320] Where the hole injecting and transporting layer is formedseparately as a hole injecting layer and a hole transporting layer, twoor more compounds are selected in a proper combination from thecompounds commonly used in hole injecting and transporting layers. Inthis regard, it is preferred to laminate layers in such an order that alayer of a compound having a lower ionization potential may be disposedadjacent the hole injecting electrode (ITO). It is also preferred to usea compound having good thin film forming ability at the hole injectingelectrode surface. The order of lamination also applies where aplurality of hole injecting and transporting layers are provided. Suchan order of lamination is effective for lowering the drive voltage andpreventing current leakage and the development and growth of dark spots.Since evaporation is utilized in the manufacture of devices, films asthin as about 1 to 10 nm can be formed uniform and pinhole-free, whichrestrains any change in color tone of light emission and a drop ofefficiency by re-absorption even if a compound having a low ionizationpotential and absorption in the visible range is used in the holeinjecting layer. Like the light emitting layer, the hole injecting andtransporting layer may be formed by evaporating the above-mentionedcompounds.

[0321] In the electron injecting and transporting layer, there may beused quinoline derivatives including organic metal complexes having8-quinolinol or a derivative thereof as a ligand such astris(8-quinolinolato)aluminum (Alq3), oxadiazole derivatives, perylenederivatives, pyridine derivatives, pyrimidine derivatives, quinoxalinederivatives, diphenylquinone derivatives, and nitro-substituted fluorenederivatives. The electron injecting and transporting layer can alsoserve as the light emitting layer. Like the light emitting layer, theelectron injecting and transporting layer may be formed by evaporationor the like.

[0322] Where the electron injecting and transporting layer is formedseparately as an electron injecting layer and an electron transportinglayer, two or more compounds are selected in a proper combination fromthe compounds commonly used in electron injecting and transportinglayers. In this regard, it is preferred to stack layers in such an orderthat a layer of a compound having a greater electron affinity may bedisposed adjacent the electron injecting electrode. The order ofstacking also applies where a plurality of electron injecting andtransporting layers are provided.

[0323] In forming the hole injecting and transporting layer, the lightemitting layer, and the electron injecting and transporting layer,vacuum evaporation is preferably used because homogeneous thin films areavailable. By utilizing vacuum evaporation, there is obtained ahomogeneous thin film which is amorphous or has a crystal grain size ofless than 0.1 μm. If the grain size is more than 0.1 μm, uneven lightemission would take place and the drive voltage of the device must beincreased with a substantial drop of hole injection efficiency.

[0324] The conditions for vacuum evaporation are not critical although avacuum of 10⁻⁴ Pa or lower and a deposition rate of about 0.01 to 1nm/sec are preferred. It is preferred to successively form layers invacuum because the successive formation in vacuum can avoid adsorptionof impurities on the interface between the layers, thus ensuring betterperformance. Also, the drive voltage of a device can be reduced and thedevelopment and growth of dark spots be restrained.

[0325] In the embodiment wherein the respective layers are formed byvacuum evaporation, where it is desired for a single layer to containtwo or more compounds, preferably boats having the compounds receivedtherein are individually temperature controlled to achieveco-deposition.

[0326] The electron injecting electrode is preferably made of metals,alloys or intermetallic compounds having a work function of up to 4 eV.With a work function of more than 4 eV, the electron injectingefficiency lowers and consequently, the light emission efficiencylowers. Examples of the metal having a work function of up to 4 eV ofwhich the electron injecting electrode film is constructed includealkali metals such as Li, Na and K, alkaline earth metals such as Mg,Ca, Sr and Ba, rare earth metals such as La and Ce, and Al, In, Ag, Sn,Zn, and Zr. Examples of the film-forming alloy having a work function ofup to 4 eV include Ag—Mg (Ag: 0.1 to 50 at %), Al—Li (Li: 0.01 to 12 at%), In—Mg (Mg: 50 to 80 at %), and Al—Ca (Ca: 0.01 to 20 at %). Thesematerials may be present alone or in combination of two or more. Wheretwo or more materials are combined, their mixing ratio is arbitrary. Itis also acceptable that an oxide or halide of an alkali metal, alkalineearth metal or rare earth metal is thinly deposited and a supportingelectrode (auxiliary electrode or wiring electrode) of aluminum etc. isused.

[0327] The electron injecting electrode may be formed by evaporation orsputtering.

[0328] The electron injecting electrode may have at least a sufficientthickness to effect electron injection, for example, a thickness of atleast 0.1 nm. Although the upper limit is not critical, the electrodethickness is typically about 0.1 to about 500 nm.

[0329] The hole injecting electrode is preferably formed of such amaterial to such a thickness that the electrode may have a transmittanceof at least 80% of emitted light. Illustratively, oxide transparentconductive thin films are preferred. For example, materials based ontin-doped indium oxide (ITO), zinc-doped indium oxide (IZO), indiumoxide (In₂O₃), tin oxide (SnO₂) or zinc oxide (ZnO) are preferable.These oxides may deviate somewhat from their stoichiometry. Anappropriate proportion of SnO₂ mixed with In₂O₃ is about 1 to 20% byweight, more preferably about 5 to 12% by weight. An appropriateproportion of ZnO₂ mixed with In₂O₃ is about 12 to 32% by weight.

[0330] The hole injecting electrode should preferably have a lighttransmittance of at least 80%, especially at least 90% in the lightemission band, typically from 350 to 800 nm, and especially at eachlight emission. Since the emitted light is generally taken out throughthe hole injecting electrode, with a lower transmittance, the lightemitted by the light emitting layer would be attenuated through theelectrode, failing to provide a luminance necessary as a light emittingdevice. It is noted that only the side from which the emitted lightexits has a transmittance of at least 80%.

[0331] The hole injecting electrode has at least a sufficient thicknessto effect hole injection, preferably a thickness of 50 to 500 nm,especially 50 to 300 nm. Although the upper limit of the electrodethickness is not critical, a too thick electrode would have the risk ofseparation. Too thin an electrode would have problems with respect tofilm strength during fabrication, hole transporting ability, andresistance value.

[0332] In depositing the hole injecting electrode, a sputtering processis preferred. The sputtering process may be a high-frequency sputteringprocess using an RF power supply although a dc sputtering process ispreferably used when the ease of control of physical properties of thehole injecting electrode being deposited and the flatness of thedeposited film are taken into account.

[0333] A protective film may be formed if necessary. The protective filmmay be formed using an inorganic material such as SiOx or an organicmaterial such as Teflon. The protective film may be either transparentor opaque and have a thickness of about 50 to 1,200 nm. Apart from thereactive sputtering process mentioned above, the protective film mayalso be formed by an ordinary sputtering or evaporation process.

[0334] Further, a sealing layer is provided on the device in order toprevent the organic layers and electrodes from oxidation. In order toprevent the ingress of moisture, the sealing layer is formed byattaching a sealing plate such as a glass plate to the substrate with anadhesive resin layer such as a commercially available low moistureabsorption photo-curable adhesive, epoxy base adhesive, silicone baseadhesive, or crosslinking ethylene-vinyl acetate copolymer adhesivesheet. Metal plates and plastic plates may also be used instead of theglass plate.

[0335] Transparent or translucent materials such as glass, quartz andresins are used as the substrate when the emitted light exits from thesubstrate side. The substrate may be provided with a color filter film,a fluorescent material-containing color conversion film or a dielectricreflecting film for controlling the color of light emission. In the caseof the inversely stacked layer structure, the substrate may be eithertransparent or opaque. For the opaque substrate, ceramic and othermaterials may be used.

[0336] The color filter film used herein may be a color filter as usedin liquid crystal displays and the like. The properties of a colorfilter may be adjusted in accordance with the light emission of theorganic EL device so as to optimize the extraction efficiency andchromatic purity.

[0337] It is also preferred to use a color filter capable of cuttingexternal light of short wavelength which is otherwise absorbed by the ELdevice materials and fluorescence conversion layer, because the lightresistance and display contrast of the device are improved.

[0338] An optical thin film such as a dielectric multilayer film may beused instead of the color filter.

[0339] Referring to FIG. 1, there is illustrated one exemplaryconstruction of the organic EL device fabricated according to theinvention. The organic EL device is shown in FIG. 1 as having on asubstrate 1, a hole injecting electrode (or anode) 2, a hole injectinglayer 3, a hole transporting layer 4, a light emitting layer 5, anelectron injecting and transporting layer 6, an electron injectingelectrode (or cathode) 7, and optionally, a protective electrode 8 inthe described order. The organic EL device of the invention is notlimited to the illustrated construction, and various other constructionsare possible depending on the desired device function. For example, theorder of lamination may be inverse to the above-described order. Thehole injecting 3, the hole transporting layer 4 and the electroninjecting and transporting layer 6 may be omitted or either one of themmay be a common layer to the light emitting layer 5.

[0340] The organic EL device of the invention is generally of the dc orpulse drive type while it can be of the ac drive type. The appliedvoltage is generally about 2 to 30 volts.

EXAMPLE

[0341] Examples of the present invention are given below together withComparative Examples for further illustrating the invention.

Example 1

[0342] On a glass substrate, a transparent ITO electrode thin film wasdeposited to a thickness of 100 nm by RF sputtering and patterned. Theglass substrate having the transparent ITO electrode was subjected toultrasonic washing with neutral detergent, acetone, and ethanol, pulledup from boiling ethanol, and dried. The transparent electrode surfacewas further cleaned with UV/ozone. Thereafter, the substrate was securedby a holder in a vacuum evaporation chamber, which was evacuated to avacuum of 1×10⁻⁵ Pa or lower.

[0343] With the vacuum kept,N,N′-diphenyl-N,N′-bis[N-(4-methylphenyl)-N-phenyl-(4-aminophenyl)]-1,1′-biphenyl-4,4′-diaminewas evaporated at a deposition rate of 0.1 nm/sec. to a thickness of 50nm, forming a hole injecting layer.

[0344] Then, N,N,N′,N′-tetrakis(m-biphenyl)-1,1′-biphenyl-4,4′-diamine(TPD) was evaporated at a deposition rate of 0.1 nm/sec to a thicknessof 20 nm, forming a hole transporting layer.

[0345] With the vacuum kept, the host material and dopant of thefollowing structural formulas were evaporated in a weight ratio of 99:1and at an overall deposition rate of 0.1 nm/sec to a thickness of 40 nm,forming a light emitting layer.

[0346] Next, with the vacuum kept, tris(8-quinolinolato)aluminum wasevaporated at a deposition rate of 0.1 nm/sec to a thickness of 20 nm,forming an electron transporting layer.

[0347] With the vacuum kept, LiF was evaporated at a deposition rate of0.01 nm/sec to a thickness of 0.3 nm, forming an electron injectingelectrode. Finally, aluminum was evaporated to a thickness of 150 nm toform a protective electrode, completing an organic EL device.

[0348] A DC voltage was applied across the organic EL device. Initially,the device was found to produce light emission to a luminance of 614cd/m² when operated at a current density of 10 mA/cm² and a drivevoltage of 5.9 volts. The current efficiency was 6.1 cd/A, the powerefficiency was 3.3 lm/W, the chromaticity coordinates (x, y) were (0.65,0.35), and the maximum luminance was 19,600 cd/m². When the device wascontinuously driven by conducting a constant current of 50 mA/cm², itexhibited an initial luminance of at least 3,200 cd/m² and a luminancehalf-life period of more than 600 hours.

Example 2

[0349] An organic EL device was prepared as in Example 1 except that thehost material in the light emitting layer was changed to the followingcompound.

[0350] A DC voltage was applied across the organic EL device. Initially,the device was found to produce light emission to a luminance of 504cd/m² when operated at a current density of 10 mA/cm² and a drivevoltage of 5.9 volts. The current efficiency was 5.0 cd/A, the powerefficiency was 2.7 lm/W, the chromaticity coordinates (x, y) were (0.64,0.36), and the maximum luminance was 11,500 cd/m². When the device wascontinuously driven by conducting a constant current of 50 mA/cm², itexhibited an initial luminance of at least 2,170 cd/m² and a luminancehalf-life period of more than 1,500 hours.

Example 3

[0351] An organic EL device was prepared as in Example 1 except that thehost material in the light emitting layer was changed to the followingcompound.

[0352] A DC voltage was applied across the organic EL device. Initially,the device was found to produce light emission to a luminance of 449cd/m² when operated at a current density of 10 mA/cm² and a drivevoltage of 5.9 volts. The current efficiency was 4.5 cd/A, the powerefficiency was 2.4 lm/W, the chromaticity coordinates (x, y) were (0.66,0.34), and the maximum luminance was 17,200 cd/m². When the device wascontinuously driven by conducting a constant current of 50 mA/cm², itexhibited an initial luminance of at least 2,440 cd/m² and a luminancehalf-life period of more than 1,500 hours.

Example 4

[0353] An organic EL device was prepared as in Example 1 except that thehost material in the light emitting layer was changed to the followingcompound.

[0354] A DC voltage was applied across the organic EL device. Initially,the device was found to produce light emission to a luminance of 441cd/m² when operated at a current density of 10 mA/cm² and a drivevoltage of 5.9 volts. The current efficiency was 4.4 cd/A, the powerefficiency was 2.3 lm/W, the chromaticity coordinates (x, y) were (0.65,0.34), and the maximum luminance was 35,200 cd/m². When the device wascontinuously driven by conducting a constant current of 50 mA/cm², itexhibited an initial luminance of at least 2,400 cd/m² and a luminanceattenuation of up to 10% after 1,000 hours and up to 15% after 4,500hours.

[0355] The host material and dopant used in this device were assessedfor excitation and fluorescence spectra, from which a Stokes shift wascomputed. The host material and dopant had a Stokes shift of 0.06 eV and0.03 eV, respectively. FIG. 2 shows excitation and fluorescence spectraof the host material and dopant. It is seen from these spectral curvesthat both the host material and dopant have vibration structures.

[0356] The temperature characteristics of the device were examined tofind the following luminance change on 10 mA/cm² constant currentdriving in various temperature ranges:

[0357] −40° C. to 20° C.: ≦10%

[0358] 20° C. to 60° C.: ≦3%

[0359] −40° C. to 60° C.: ≦13%.

[0360] After 500 hours of continuous driving at 85° C., the deviceexhibited a luminance change of up to 10% and a drive voltage change ofless than 2 V.

Example 5

[0361] An organic EL device was prepared as in Example 1 except that thehost material in the light emitting layer was changed to the followingcompound.

[0362] A DC voltage was applied across the organic EL device. Initially,the device was found to produce light emission to a luminance of 296cd/m² when operated at a current density of 10 mA/cm² and a drivevoltage of 6.7 volts. The current efficiency was 3.0 cd/A, the powerefficiency was 1.4 lm/W, the chromaticity coordinates (x, y) were (0.60,0.38), and the maximum luminance was 16,500 cd/m². When the device wascontinuously driven by conducting a constant current of 79 mA/cm², itexhibited an initial luminance of at least 2,400 cd/m² and a luminancehalf-life period of more than 300 hours.

Example 6

[0363] An organic EL device was prepared as in Example 1 except that thehost material in the light emitting layer was changed to the followingcompound.

[0364] A DC voltage was applied across the organic EL device. Initially,the device was found to produce light emission to a luminance of 267cd/m² when operated at a current density of 10 mA/cm² and a drivevoltage of 6.6 volts. The current efficiency was 2.7 cd/A, the powerefficiency was 1.3 lm/W, the chromaticity coordinates (x, y) were (0.55,0.37), and the maximum luminance was 12,860 cd/m². When the device wascontinuously driven by conducting a constant current of 97 mA/cm², itexhibited an initial luminance of at least 2,400 cd/m² and a luminancehalf-life period of more than 300 hours.

Example 7

[0365] An organic EL device was prepared as in Example 1 except that thehost material in the light emitting layer was changed to the followingcompound.

[0366] A DC voltage was applied across the organic EL device. Initially,the device was found to produce light emission to a luminance of 260cd/m² when operated at a current density of 10 mA/cm² and a drivevoltage of 6.7 volts. The current efficiency was 2.6 cd/A, the powerefficiency was 1.2 lm/W, the chromaticity coordinates (x, y) were (0.64,0.36), and the maximum luminance was 8,780 cd/m². When the device wascontinuously driven by conducting a constant current of 95 mA/cm², itexhibited an initial luminance of at least 2,400 cd/m² and a luminancehalf-life period of more than 300 hours.

Example 8

[0367] An organic EL device was prepared as in Example 1 except that thehost material in the light emitting layer was changed to a mixture ofthe following compounds in a weight ratio of 9:1 (the former compound isthe same as used in Example 4).

[0368] The host material (mixture) and the dopant were evaporated in aweight ratio of 99:1 and at an overall deposition rate of 0.1 nm/sec toa thickness of 40 nm, forming a light emitting layer.

[0369] A DC voltage was applied across the organic EL device. Initially,the device was found to produce light emission to a luminance of 494cd/m² when operated at a current density of 10 mA/cm² and a drivevoltage of 5.9 volts. The current efficiency was 4.9 cd/A, the powerefficiency was 2.6 lm/W, and the chromaticity coordinates (x, y) were(0.65, 0.34). When the device was continuously driven by conducting aconstant current of 50 mA/cm², it exhibited an initial luminance of atleast 2,640 cd/m² and a luminance attenuation of up to 10% after 2,000hours.

Example 9

[0370] An organic EL device was prepared as in Example 8 except that theweight ratio of the host compounds in the light emitting layer waschanged to 7.5:2.5.

[0371] A DC voltage was applied across the organic EL device. Initially,the device was found to produce light emission to a luminance of 510cd/m² when operated at a current density of 10 mA/cm² and a drivevoltage of 6 volts. The current efficiency was 5.1 cd/A, the powerefficiency was 2.8 lm/W, and the chromaticity coordinates (x, y) were(0.65, 0.34). When the device was continuously driven by conducting aconstant current of 50 mA/cm², it exhibited an initial luminance of atleast 2,330 cd/m² and a luminance attenuation of up to 10% after 2,000hours.

Example 10

[0372] An organic EL device was prepared as in Example 8 except that theweight ratio of the host compounds in the light emitting layer waschanged to 5:5.

[0373] A DC voltage was applied across the organic EL device. Initially,the device was found to produce light emission to a luminance of 534cd/m² when operated at a current density of 10 mA/cm² and a drivevoltage of 5.9 volts. The current efficiency was 5.3 cd/A, the powerefficiency was 2.8 lm/W, and the chromaticity coordinates (x, y) were(0.65, 0.35). When the device was continuously driven by conducting aconstant current of 50 mA/cm², it exhibited an initial luminance of atleast 2,391 cd/m² and a luminance attenuation of up to 10% after 2,000hours.

Example 11

[0374] An organic EL device was prepared as in Example 1 except that thehost material and the dopant in the light emitting layer were changed tothe following compounds.

[0375] The host material and the dopant were evaporated in a weightratio of 99:1 and at an overall deposition rate of 0.1 nm/sec to athickness of 40 nm, forming a light emitting layer. The dopant materialhad to be heated at 460° C. or higher for purification by sublimation.

[0376] A DC voltage was applied across the organic EL device. Initially,the device was found to produce light emission to a luminance of 505cd/m² when operated at a current density of 10 mA/cm² and a drivevoltage of 5.7 volts. The current efficiency was 5.1 cd/A, the powerefficiency was 2.8 lm/W, and the chromaticity coordinates (x, y) were(0.65, 0.35). When the device was continuously driven by conducting aconstant current of 50 mA/cm², it exhibited an initial luminance of atleast 2,330 cd/m² and a luminance attenuation of up to 30% after 1,700hours.

Example 12

[0377] An organic EL device was prepared as in Example 1 except that thehost material and the dopant in the light emitting layer were changed tothe following compounds.

[0378] The host material and the dopant were evaporated in a weightratio of 99:1 and at an overall deposition rate of 0.1 nm/sec to athickness of 40 nm, forming a light emitting layer.

[0379] A DC voltage was applied across the organic EL device. Initially,the device was found to produce light emission to a luminance of 438cd/m² when operated at a current density of 10 mA/cm² and a drivevoltage of 6 volts. The current efficiency was 4.4 cd/A, the powerefficiency was 2.3 lm/W, and the chromaticity coordinates (x, y) were(0.65, 0.35). When the device was continuously driven by conducting aconstant current of 50 mA/cm², it exhibited an initial luminance of atleast 2,650 cd/m² and a luminance attenuation of up to 10% after 2,300hours.

Example 13

[0380] An organic EL device was prepared as in Example 1 except that thehost material and the dopant in the light emitting layer were changed tothe following compounds.

[0381] The host material and the dopant were evaporated in a weightratio of 99:1 and at an overall deposition rate of 0.1 nm/sec to athickness of 40 nm, forming a light emitting layer.

[0382] The host material and dopant used in this device were assessedfor excitation and fluorescence spectra, from which a Stokes shift wascomputed. The host material had a Stokes shift of 0.24 eV. It is seenfrom the spectral curves that both the host material and dopant havevibration structures.

[0383] The temperature characteristics of the device were examined tofind the following luminance change in various temperature ranges:

[0384] −40° C. to 20° C.: ≦−4%

[0385] 20° C. to 60° C.: ≦−3%

[0386] −40° C. to 60° C.: ≦−7%.

Example 14

[0387] An organic EL device was prepared as in Example 1 except that thehost material and the dopant in the light emitting layer were changed tothe following compounds.

[0388] The host material and the dopant were evaporated in a weightratio of 99:1 and at an overall deposition rate of 0.1 nm/sec to athickness of 40 nm, forming a light emitting layer. It is noted that thedopant material could be purified by sublimation at a temperature below360° C.

[0389] A DC voltage was applied across the organic EL device. Initially,the device was found to produce light emission to a luminance of 660cd/m² when operated at a current density of 10 mA/cm² and a drivevoltage of 5.6 volts. The current efficiency was 6.6 cd/A, the powerefficiency was 3.7 lm/W, and the chromaticity coordinates (x, y) were(0.65, 0.35). The maximum luminance was 55,000 cd/m². When the devicewas continuously driven by conducting a constant current of 50 mA/cm²,it exhibited an initial luminance of at least 3,530 cd/m² and aluminance attenuation of up to 10% after 500 hours.

Example 15

[0390] An organic EL device was prepared as in Example 1 except that thehost material and the dopant in the light emitting layer were changed tothe following compounds.

[0391] The host material and the dopant were evaporated in a weightratio of 99:1 and at an overall deposition rate of 0.1 nm/sec to athickness of 40 nm, forming a light emitting layer. It is noted that thedopant material could be purified by sublimation at a temperature below360° C.

[0392] A DC voltage was applied across the organic EL device. Initially,the device was found to produce light emission to a luminance of 764cd/m² when operated at a current density of 10 mA/cm² and a drivevoltage of 6 volts. The current efficiency was 7.6 cd/A, the powerefficiency was 4.0 lm/W, and the chromaticity coordinates (x, y) were(0.65, 0.35). The maximum luminance was 24,500 cd/m². When the devicewas continuously driven by conducting a constant current of 50 mA/cm²,it exhibited an initial luminance of at least 4,200 cd/m² and aluminance attenuation of up to 10% after 500 hours.

Comparative Example 1

[0393] An organic EL device was prepared as in Example 1 except that thehost material in the light emitting layer was changed to the followingcompound.

[0394] A DC voltage was applied across the organic EL device. Initially,the device was found to produce light emission to a luminance of 160cd/m² when operated at a current density of 10 mA/cm² and a drivevoltage of 6.9 volts. The current efficiency was 1.6 cd/A, the powerefficiency was 0.7 lm/W, the chromaticity coordinates (x, y) were (0.61,0.37), and the maximum luminance was 9,570 cd/m². When the device wascontinuously driven by conducting a constant current of 145 mA/cm², itexhibited an initial luminance of at least 2,400 cd/m² and a luminancehalf-life period of less than 300 hours.

Comparative Example 2

[0395] An organic EL device was prepared as in Example 4 except that thehost material and the dopant in the light emitting layer were changed tothe following compounds.

[0396] The host material and the dopant were evaporated in a weightratio of 97:3 and at an overall deposition rate of 0.1 nm/sec to athickness of 40 nm, forming a light emitting layer.

[0397] The host material and dopant used in this device were assessedfor excitation and fluorescence spectra, from which a Stokes shift wascomputed. The host material and dopant had a Stokes shift of 0.2 eV and0.31 eV, respectively. FIG. 3 shows excitation and fluorescence spectraof the host material and dopant. It is seen from the spectral curvesthat the dopant does not have a vibration structure in the excitationspectrum, and the host material does not have a vibration structure inthe fluorescence spectrum.

[0398] The temperature characteristics of the device were examined tofind the following luminance change on 10 mA/cm² constant currentdriving in various temperature ranges:

[0399] −40° C. to 20° C.: ≧−12%

[0400] 20° C. to 60° C.: ≧−9%

[0401] −40° C. to 60° C.: ≧−21%.

Comparative Example 3

[0402] An organic EL device was prepared as in Example 4 except that thehost material and the dopant in the light emitting layer were changed tothe following compounds.

[0403] The host material and the dopant were evaporated in a weightratio of 99:1 and at an overall deposition rate of 0.1 nm/sec to athickness of 40 nm, forming a light emitting layer.

[0404] The host material and dopant used in this device were assessedfor excitation and fluorescence spectra, from which a Stokes shift wascomputed. The host material and dopant had a Stokes shift of 0.2 eV and0.31 eV, respectively. It is seen from the spectral curves that neitherthe host material nor the dopant has a vibration structure.

[0405] The temperature characteristics of the device were examined tofind the following luminance change in various temperature ranges:

[0406] −40° C. to 20° C.: ≧31%

[0407] 20° C. to 60° C.: ≧18%

[0408] −40° C. to 60° C.: ≧49%.

[0409] There has been described an organic EL device which emits lightto a satisfactory luminance, especially in a long wavelength region, isoperated at a constant voltage, and has a sufficient durability tomaintain satisfactory light emission performance over a long period oftime, experience a minimal voltage rise during continuous operation, andundergo a minimal degradation on driving at elevated temperature.Especially when a red light emitting device is fabricated, it has a highchromatic purity because the host produces little light emission. Over awide temperature region, the device produces a consistent luminance withminimal changes of efficiency. The device can produce linear luminancecharacteristics in proportion to current flow over a wide current regioncovering from the low current region for use in TFT driving to the highcurrent region for use in simple matrix driving and thus provide asatisfactory tone display.

[0410] Although some preferred embodiments have been described, manymodifications and variations may be made thereto in light of the aboveteachings. It is therefore to be understood that the invention may bepracticed otherwise than as specifically described without departingfrom the scope of the appended claims.

[0411] This application is based on Japanese patent applications JP2000-121724, filed Apr. 21, 2000, and JP 2001-121664, filed Apr. 19,2001, the entire contents of each of which are hereby incorporated byreference, the same as if set forth at length.

What is claimed is:
 1. An organic EL device comprising one or moreorganic layers between a pair of electrodes participating in at least alight emitting function, at least one of the organic layers containingat least one of organic compounds having basic skeletons of thefollowing formulas (I) to (IV) and at least one organic compound havinga skeleton of the following formula (V) at the same time:

 wherein Q¹ to Q⁸ are independently hydrogen or substituted orunsubstituted alkyl, aryl, amino, heterocyclic or alkenyl radicals,

 wherein R₁, R₂, R₃ and R₄ are independently aryl, fluorene, carbazolyl,alkyl, alkoxy, aryloxy, amino or halogen radicals, at least one of R₁,R₂, R₃ and R₄ is aryl, r1, r2, r3 and r4 each are 0 or an integer of 1to 5, with the proviso that r1, r2, r3 and r4 are not 0 at the sametime, R₅ and R₆ are independently alkyl, alkoxy, amino, aryl or halogenradicals and may be the same or different, r5 and r6 each are 0 or aninteger of 1 to 4,

 wherein A₁₀₁ is a monophenylanthryl or diphenylanthryl radical and maybe the same or different, L is hydrogen, a single bond or an n-valentlinkage, and n is an integer of 1 to 4, Q_(n)-L₁₀₁  (IV)  wherein Q is apyrazinyl radical having fused thereto a six-membered aromatic ringcontaining 0 to 2 nitrogen atoms and may be the same or different, n is2 or 3, and L₁₀₁ is a single bond or n-valent radical,

 wherein X₁ to X₁₀, L₁ and L₂ are independently hydrogen, halogen atoms,straight, branched or cyclic alkyl radicals which may have substituents,straight, branched or cyclic alkoxy radicals which may havesubstituents, straight, branched or cyclic alkylthio radicals which mayhave substituents, straight, branched or cyclic alkenyl radicals whichmay have substituents, straight, branched or cyclic alkenyloxy radicalswhich may have substituents, straight, branched or cyclic alkenylthioradicals which may have substituents, substituted or unsubstitutedaralkyl radicals, substituted or unsubstituted aralkyloxy radicals,substituted or unsubstituted aralkylthio radicals, substituted orunsubstituted aryl radicals, substituted or unsubstituted aryloxyradicals, substituted or unsubstituted arylthio radicals, substituted orunsubstituted amino radicals, cyano, hydroxyl, —COOR¹ radicals (whereinR¹ is hydrogen, a substituted or unsubstituted straight, branched orcyclic alkyl radical, a substituted or unsubstituted straight, branchedor cyclic alkenyl radical, a substituted or unsubstituted aralkylradical or a substituted or unsubstituted aryl radical), —COR² radicals(wherein R² is hydrogen, a substituted or unsubstituted straight,branched or cyclic alkyl radical, a substituted or unsubstitutedstraight, branched or cyclic alkenyl radical, a substituted orunsubstituted aralkyl radical, a substituted or unsubstituted arylradical or an amino radical), or —OCOR³ radicals (wherein R³ is asubstituted or unsubstituted straight, branched or cyclic alkyl radical,a substituted or unsubstituted straight, branched or cyclic alkenylradical, a substituted or unsubstituted aralkyl radical, or asubstituted or unsubstituted aryl radical), or at least two adjoiningradicals selected from X₁ to X₁₀, L₁ and L₂ may bond or fuse together toform a substituted or unsubstituted carbocyclic aliphatic ring, aromaticring or fused aromatic ring with the carbon atoms to which they areattached, or L₁ and L₂ each may be a single bond. n is 1 or
 2. 2. Theorganic EL device of claim 1 wherein the at least one of the organiclayers contains a host material and a dopant, said host materialcomprises at least one compound selected from the organic compoundshaving basic skeletons of the formulas (I) to (IV) and said dopantcomprises at least one compound selected from the organic compoundshaving a skeleton of the formula (V).
 3. The organic EL device of claim1 or 2 wherein in formula (V), at least two adjoining radicals selectedfrom X₁ to X₁₀, L₁ and L₂ bond or fuse together to form a substituted orunsubstituted carbocyclic aliphatic ring, aromatic ring or fusedaromatic ring with the carbon atoms to which they are attached.
 4. Theorganic EL device of any one of claims 1 to 3 wherein the compound offormula (V) is a compound of the following formula (VI):

wherein X₁ to X₆, X₉, X₁₀, X₁₁ to X₁₆, X₁₉ and X₂₀ are independentlyhydrogen, halogen atoms, straight, branched or cyclic alkyl radicalswhich may have substituents, straight, branched or cyclic alkoxyradicals which may have substituents, straight, branched or cyclicalkylthio radicals which may have substituents, straight, branched orcyclic alkenyl radicals which may have substituents, straight, branchedor cyclic alkenyloxy radicals which may have substituents, straight,branched or cyclic alkenylthio radicals which may have substituents,substituted or unsubstituted aralkyl radicals, substituted orunsubstituted aralkyloxy radicals, substituted or unsubstitutedaralkylthio radicals, substituted or unsubstituted aryl radicals,substituted or unsubstituted aryloxy radicals, substituted orunsubstituted arylthio radicals, substituted or unsubstitutedarylalkenyl radicals, substituted or unsubstituted alkenylaryl radicals,substituted or unsubstituted amino radicals, cyano, hydroxyl, —COOR¹radicals (wherein R¹ is hydrogen, a substituted or unsubstitutedstraight, branched or cyclic alkyl radical, a substituted orunsubstituted straight, branched or cyclic alkenyl radical, asubstituted or unsubstituted aralkyl radical or a substituted orunsubstituted aryl radical), —COR² radicals (wherein R² is hydrogen, asubstituted or unsubstituted straight, branched or cyclic alkyl radical,a substituted or unsubstituted straight, branched or cyclic alkenylradical, a substituted or unsubstituted aralkyl radical, a substitutedor unsubstituted aryl radical or an amino radical), or —OCOR³ radicals(wherein R³ is a substituted or unsubstituted straight, branched orcyclic alkyl radical, a substituted or unsubstituted straight, branchedor cyclic alkenyl radical, a substituted or unsubstituted aralkylradical, or a substituted or unsubstituted aryl radical), or at leasttwo adjoining radicals selected from X₁ to X₂₀ may bond together to forma substituted or unsubstituted carbocyclic aliphatic ring, aromatic ringor fused aromatic ring with the carbon atoms to which they are attached.5. The organic EL device of claim 4 wherein the compound of formula (VI)is a compound of the following formula (VI′):

wherein X₁ to X₄₄ are as defined for X₁ to X₂₀ in formula (VI).
 6. Theorganic EL device of claim 4 or 5 wherein X₁ to X₂₀ in formula (VI) andX₁ to X₄₄ in formula (VI′) are independently substituted orunsubstituted aryl, alkyl, alkenyl, alkoxy or aryloxy radicals.
 7. Theorganic EL device of any one of claims 4 to 6 wherein at least one of X₁to X₂₀ in formula (VI) and X₁ to X₄₄ in formula (VI′) is anortho-substituted phenyl radical.
 8. The organic EL device of any one ofclaims 4 to 7 wherein in formula (VI) or (VI′), either one or both of X₁and X₄ and/or either one or both of X₁₁ and X₁₄ are ortho-substitutedphenyl radicals.
 9. The organic EL device of any one of claims 1 to 8wherein said at least one of the organic layers contains at least oneorganic compound having a basic skeleton of the formula (I).
 10. Theorganic EL device of any one of claims 1 to 9 wherein said at least oneof the organic layers contains at least one organic compound having abasic skeleton of the formula (I) and at least one organic compoundhaving a basic skeleton of the formula (II) at the same time.
 11. Theorganic EL device of any one of claims 4 to 10 wherein at least one ofthe organic compounds has a vibration structure in both an excitationspectrum and a fluorescence spectrum.
 12. The organic EL device of anyone of claims 4 to 11 wherein at least one of the organic compounds hasa Stokes shift of up to 0.1 eV.
 13. The organic EL device of any one ofclaims 4 to 12 wherein the host material in a light emitting layer has agreater electron affinity than an electron transporting layer and/or ahole transporting layer.
 14. The organic EL device of any one of claims1 to 13 wherein the organic compound having a basic skeleton of theformula (I) is one wherein at least two of Q¹ to Q⁸ are substituted orunsubstituted aryl radicals.
 15. The organic EL device of claim 14wherein the organic compound having a basic skeleton of the formula (I)is one wherein at least six of Q¹ to Q⁸ are substituted or unsubstitutedaryl radicals.
 16. The organic EL device of claim 14 or 15 wherein theorganic compound having a basic skeleton of the formula (I) is onewherein at least two of Q¹, Q², Q³ and Q⁴ are substituted orunsubstituted aryl radicals.
 17. The organic EL device of any one ofclaims 14 to 16 wherein the organic compound having a basic skeleton ofthe formula (I) is one wherein at least four of Q¹, Q², Q³ and Q⁴ aresubstituted or unsubstituted aryl radicals.
 18. The organic EL device ofany one of claims 14 to 17 wherein at least two of the aryl radicalsrepresented by Q¹, Q², Q³ and Q⁴ have aryl radicals substituted thereon.19. The organic EL device of any one of claims 2 to 18 wherein the atleast one of the organic layers contains 80 to 99.9% by weight of thehost material.
 20. An organic EL device wherein at least one of organiclayers contains at least one organic compound having a basic skeleton ofthe formula (I) as set forth in claim 16 and at least one organiccompound having a basic skeleton of the formula (IV′).
 21. The organicEL device of any one of claims 1 to 20, further comprising at least onehole injecting and transporting layer.
 22. The organic EL device of anyone of claims 1 to 21, further comprising at least one electroninjecting and transporting layer.
 23. An organic EL device comprisingone or more organic layers between a pair of electrodes participating inat least a light emitting function, wherein the one or more organiclayers contain organic compounds, at least one of which has a vibrationstructure in both an excitation spectrum and a fluorescence spectrum.24. An organic EL device comprising one or more organic layers between apair of electrodes participating in at least a light emitting function,wherein the one or more organic layers contain organic compounds, atleast one of which has a Stokes shift of up to 0.1 eV.
 25. The organicEL device of claim 24 wherein a host material in a light emitting layerhas a greater electron affinity than an electron transporting layerand/or a hole transporting layer.